


When Angels and Demons Fall in Love!

by Winchestersister1313



Category: Supernatural
Genre: Alternate Universe - High School, Angels, Demons, F/M, Fluff and Smut, M/M, Private School, powers
Language: English
Status: Completed
Published: 2019-05-25
Updated: 2019-06-20
Packaged: 2020-03-17 07:15:58
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 11
Words: 38,060
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18960466
Author URL: https://archiveofourown.org/users/Winchestersister1313/pseuds/Winchestersister1313
Summary: Dean and Olive Winchester are the children of John Winchester. The powerful head of the demon faction in Kansas, John was strong with broad wings and a thick tail, all the signs of a tough demon. His son was no different at sixteen he wasn’t as tall but he hadbroad wings and a long tail, Dean had shining  green-eyes. His sister was beautiful and would follow Dean to the ends of the earth. She was smaller, with sleek wings and tail longer than any other demons. She also had small black horns protruding from her forehead, the pair were both rebellious and one day John decided he was done with their disobedience and decided to send them both off to boarding school.





	1. Chapter 1

**Author's Note:**

> Betaed by JenSpinner

The angels and demons have been trying to get along better since they realized that if they didn't stop the senseless fighting, they would end up wiping each other out as they had already done to the humans centuries ago. Both sides decided enough was enough, and if they all really wanted to survive, they all needed to work together, have their children and their children work together. Once they started talking, both sides noticed that they had more in common than they ever realized. Angels had necessary powers left after years of not going back to heaven, and it dwindled with each generation, healing and telekinesis were about all they had left power-wise. Demons were worse off. They had necessary teleportation, some healing depending on the family, the more influential the family, the better off they were. A few who were lucky enough to be born with horns harnessed power long forgotten by both sides.  
   
Many have started having interspecies relationships. They even opened a boarding school for angels and demons to attend together. The idea is that they could learn from each other, one individual from each species would be paired with an individual from the other so they could create lasting friendships and strengthen the fragile truce between both species.  
   
Dean and Olive Winchester are the children of John Winchester. The influential head of the demon faction in Kansas, John was keen with broad wings and a thick tail, all the signs of a mighty demon. His son was no different at sixteen he wasn't as tall, but he had broad wings and a long tail, Dean had shining green-eyes. His sister was beautiful and would follow Dean to the ends of the earth. She was smaller, with sleek wings and tail longer than any other demons. She also had small black horns protruding from her forehead. The pair were both rebellious; one day, John was done with their disobedience and decided to send them both off to boarding school.  
   
"We will go, but are we rooming together, Dad, please?" Olive begged  
   
"I already talked to the school and told them, and they said it was fine. They have a set of angel twins that need to stay together, too, so you'll all room together," John said  
   
"I don't know why we need to room with those cloud hoppers!?" Dean said  
"Why? Because we all need to try to get along!" John said Dean rolled his eyes.  
   
They arrived at the academy the next day suitcases and boxes in hand.  
Olive could teleport and luckily could take others with her when did, so it only took them a few seconds to get to the school, which looked a college campus, significant buildings with ivy crawling up their sides, big weeping willows lined the walkway.  
   
"I'm kind of excited to be here!" Olive said  
   
"Yeah, O so exciting!" Dean said Olive shoved him  
"Shut up!" She said following him across the grass towards, the table set up for new demons  
   
"Hello. Names Crowley!" Said a little British demon with stocky wings.  
   
"Uh hi, Dean and Olive Winc.."  
   
"Winchester, I know!" Crowley said, looking down his clipboard and ticking off their names.  
   
"You're in room two hundred and fifteen," He said handing Dean the keys, as they headed towards they buildings marked dorms, wisteria climbed up and around the door, the halls were busy with new and old students talking to each other. Dean looked at Olive and gave her soft smile, they really didn't wanna be there, but they were making the best of the situation, they reached the room the door was open, but no one was in there one side of the room was entirely made bunk beds two sets of books, pencils perfectly lined up on the desk, shoes lined up by the bottom bunk.  
   
"Well, shit, you never know we may get along with them," Olive said of their angel roommates. They put their stuff away and headed to the dining hall.  
   
As they walked down the hall the angels snickered, Olive always tried to hide her horns, no matter how much Dean always wanted to make her feel confident about them, the fact was that not many demons had them, so she was what Dean called 'unique,' what some called… weird.  
   
"Dean, are they…."  
   
"Ignore them. They don't know you!" Dean said, wrapping a protective arm around his sister, Olive was still a bit insecure about her horns and needed her brother.  
   
"what are you looking at!?" Dean said to the angel that was laughing. Dean's tail twitched back and forth in irritation as he glared at the angel.  
   
"Nothing," Said the angel, holding up his hands in mock surrender.  
   
"Keep it that way!" Dean said, glancing down at Olive.  
"Welcome on your first day to our new students!" The headmaster said, "my name is Victor Hendrickson, as you all know this school is about equality, we operate a program that is dedicated to peace and getting along learning to respect each other, angels and demons alike!" He said, and he pointed toward Dean and Olive, "we are lucky to welcome the twins from both factions head families, demon, and angel! Now you all know your classes, if anyone is unsure of anything please ask a member of the staff. You are now free to mingle and get to know your new classmates. Dinner will be served soon!"  
   
"I should have covered them!" Olive said to Dean, self consciously.  
   
"No way O, your horns make you unique you're not like every other demon out there, you're special!" Dean said she gave him a half-smile.  
   
"I'm gonna go back to the room, can you let me know when the foods ready!" She said  
   
"Are you sure?" He asked, she nodded and left, keeping her head down.  
   
"Hey, where are you going?" A guy with tall, strong leathery wings and his tail wrapped around his leg asked her.  
   
"Back to my room" Olive said  
   
"I'm Michael!"  
   
"Olive, my brother calls me O!" She said blushing, her tail was swishing slightly, so she grabbed it, and it wrapped around her arm.  
   
"There's a party tomorrow you should come, bring your brother!" Michael said  
   
"Thanks, we'd like that!" Olive said smiling  
   
"I have never met a shy demon before!" He said reaching out to touch he arm  
   
"I'm gonna go...now!" She said slowly walking away  
   
"It was nice to meet you."  
   
"You too," She called back.  
   
Dean was watching his sister talk to Michael, smiling that she may have made a new friend.  
   
"You really gonna let your girl flirt with Michael?" She asked  
   
"First not my girl she's my sister, second how do you know his name?" Dean asked  
"Everyone knows Michael, I'm Charlie!" She said. She had short red hair, her wings were rather small, and she had a slim tail.  
   
"Dean, that was my twin sister Olive or as I like to call her O!" Dean said  
   
"Why, O? Why not Ollie? She seems sweet" Charlie said  
   
"I don't know our mom called her that she would say Oh O!"  
   
"Yeah. So it stuck!" Dean said  
   
"That's cute. See ya around Dean," Charlie said, walking away.  
   
When Olive got to the room, the door was shut but not locked, and she walked, noticing that she had just in on two naked angels toweling off.  
   
"Oh my god! I'm so sorry!" She squealed, turning away from them and covering her eyes.  
   
"Will you shut the door?" One asked  
   
"I'm so sorry! I'm gonna hide under my covers now!" She said as closing the door, hurried to her bed. Olive hid her face covers until the angels were dressed, they didn't say anything to her but spoke to each other in Enochian.  
   
"That's Enochian!" Olive said from behind her blanket.  
   
"Do you understand us?"  
   
"No," Olive said  
   
"I'm Olive by the way!" She said from under her blankets, her tail snaked out and gave a small wave and quickly retreated to the safety of the sheets.  
   
"You can look now!" One of the angels said, and she peeked out from under the covers.  
   
"I'm James, and he's Castiel!" Said the angel that had spoken who was now pointing to his brother.   
   
"Nice to meet you!" She said, staring at them, they were identical twins, not too tall, dark hair, incredibly fluffy, jet black wings blue eyes.  
   
"I'm staring, that's rude!" She said, suddenly wishing Dean was with her.  
   
"Ya I…. damnit Olive!" Dean said suddenly appearing out of thin air.  
"I'm sorry. I didn't mean too, I got nervous!" She said apologetically  
   
"Uh hi," Dean said to the angels as he sat next to his sister "I know this is a lot for you, dad should have let you stay home!"  
   
"No, he knows me, I can summon you at will and you to me, it wouldn't have worked, that's James and Castiel," She said  
   
"Hello!" They said in unison.  
   
"Cool, since your both here, stay on your side. Don't touch our stuff, we will stay out of your hair, you stay out of ours and just leave Olive alone!" Dean said his tail wrapping and unwrapping around his leg.  
   
"Be nice, they didn't do anything."  
   
"You wouldn't have summoned me here if they didn't," He said  
   
"I walked while they were naked. I got embarrassed. I'm sorry, it was my fault" She said  
   
"I'm sorry! She's my sister!" He said as his tail settled.  
   
"It's fine we understand," They said  
   
"I was talking to a beautiful demon," Huffed Dean at his sister "Are you sure you're ok?"  
   
"Yeah!" She said so Dean nodded, and with one last glance at the angels, he left.  
   
"I'm sorry!" Dean said finding the demon he was talking to earlier.  
   
"What happened?" She asked  
   
"My sister and I can summon each other at will, she's introverted and sometimes when she gets nervous, and she summons me by accident!" Said Dean.  
   
"Wow, that's really cool! Is it true she has horns?" The demon asked  
   
"Yeah, why?" Dean asked  
   
"I've just never seen a demon with horns," She said  
   
"Lisa, my sister, isn't a freak show, she's a demon, and sensitive about her horns so please don't bring them up!" Dean said  
   
"I'm sorry I didn't know!" She said, wrapping her tail around his wrist.  
"We should head to the dining hall!" Olive said and disappeared  
   
"Well, I guess that answers that question!" James said, looking at his brother.  
   
"She seems nicer than her brother!" Castiel said James nodded in agreement as they left the room.  
   
"Hey. What did I miss?" Olive asked, taking her seat next to Dean.  
   
"This is Lisa," Dean said  
   
"Hello, sorry about earlier!" Olive said  
   
"No worries Dean explained," Said, Lisa.  
   
"Oh," She said shifting  
   
"I really like your horns," Lisa said Olive blushed a deep red and hid her face  
   
"I told you not to bring them up" Dean hissed at Lisa angrily.  
   
"Everyone is staring at them, aren't they?" Olive asked  
   
"No, and if they are, they have me to deal with!" Dean said  
   
"I heard demons with horns are like super powerful and can like to bend things to their will!" Lisa said, seemingly choosing to ignore Dean's warnings not to talk about them.  
   
"Um ok. I've never heard that before" Olive said, looking at Dean he shrugged, Olive looked at her food.  
   
"What do you want?" Lisa asked, making Dean and Olive look up to see who she was talking to.  
   
"We were wondering, Olive if you wanted to come to eat with us?" James asked  
   
"And why would she want to do that?" Lisa responded before Olive could even get a word out.  
   
"I can make my own choices and stop being rude. Maybe next time, but thank you!" Olive said, shooting a look at Lisa.  
   
After dinner Dean wanted to go to Lisa's room, "I'm just gonna go back to our room get ready for class on Monday" Olive said  
"Oh, and... um, Michael invited us to a party tomorrow night."  
   
"What did you say?" Dean asked  
   
"Yes, actually," Olive said  
   
"I'm proud of you sis!" Dean said smiling  
   
"Don't do anything I wouldn't!" She said, waving him off and laughing as she walked away.  
   
She went to their room, the angel twins, Castiel and James weren't there, so she gathered up her stuff for a shower and headed down the hall to the girl's restroom. Olive got in a stall took off her clothes, while the bath heated up.  
   
"I have never seen a horned demon in my life" Olive heard other demons talking about her, she was annoyed t that other demons found it necessary to talk about her just because she has horns, it's not her fault she was born this way.  
   
"My dad said she got them from her mom's side, and their mom had horns too!" A second voice reached Olive, and she listened, feeling both angry and hurt.  
   
"Have you seen both of them?" The first girl's voice asked.  
   
"Yeah, they are called the green-eyed demons. Apparently, Dean likes to get into trouble, and he drags his sister along for the ride!" The second girl said  
   
"How do you know that!" The first girl asked her friend.  
   
"I have my sources!" The other girl said with a giggle.  
   
"That just makes them hotter" Olive huffed to herself and turned off the shower, she wrapped a towel around her and exited the shower stall. The door bumped against the booth causing the two other demons to look up at her, with guilty expressions.  
   
"Oh shit!" The first girl said when she saw Olive standing there looking annoyed.  
   
"Maybe next time keep it down when you're talking about someone, or at least have the sense to check you can't be overheard first," Olive said bitterly before heading back to her room, no one was in there so Olive got dressed quickly. She was trying to dry her wings when James and Castiel walked in.  
   
"We're sorry," They both said, then they all chuckled as they realized this was how she'd walked in on them earlier.  
   
"It's ok. I'm just trying to dry my wings, and I can't quite reach them" Olive said staining,  
"I flap them a few times, but it's not just my room, and I didn't want to get your stuff wet!" She said thoughtfully.  
   
"Hey, O!" Dean said coming in the room  
   
"We all really need to start knocking." Laughed Olive, then she turned to Dean "Help me please?" She said, holding out her towel. James and Castiel went to their side of the room, trying to keep out of Dean's way.  
   
"People were talking shit about us in the shower!" Olive said quietly to her brother.  
"What were they saying?" Dean asked wiping the water droplets off her wings.  
   
"Stupid stuff. I thought you were going to Lisa's room!" Olive said, taking her towel and hanging it up.  
   
"Yeah, she's a little aggressive!" Dean said  
   
"Did she touch your tail?" Olive asked with a smirk  
"No, she wrapped hers around my wrist!" Dean said  
"Oh, that's gross!" Olive said Dean nodded  
   
"Let me get your horns, you still have soap under them,  
"I'll be back!" Dean said, grabbing a washcloth.  
   
"Um, can I ask a question?" Castiel asked almost timidly  
"As long as it's not about my horns" Said Olive bluntly.  
"No it's not about your horns, it's the tail thing!" Castiel said  
   
"Well it's an appendage you know, but it's also susceptible, we aren't supposed to touch someone else's tail without permission, and we really shouldn't touch people who aren't mates or family with them!" Olive said as her tail snaked around her waist, coiling, and uncoiling as if to make a point.  
   
"Oh, like our wings!" Castiel said thoughtfully.  
"Exactly!" Olive said, at that moment, Dean came back into the room, and Castiel looked down and went back to reading a book on his bed.  
"Come here," Dean said, motioning towards the bed "Every time O!"  
   
"You know I have a hard time keeping them clean, besides mom used to help me, you know that!" Olive said flicking her tail  
"It's ok, I got you," Dean said kindly.  
   
"Ow careful, you know they are sensitive!" Olive said flinching away from Dean as he rubbed at her horns with a dry cloth.  
   
"I'm sorry. I didn't mean to be so rough!" Dean said, he moved forward again and carefully wiped the drying soap from around Olive's horns. "Done," He declared after another few moments.  
   
"Thanks, Dean, you're the best!" She said smiling  
   
"Shut up!" He said, "I think I got it all anyway."  
Olive and Dean talked for a while about their classes, working out which ones they had together, James and Castiel kept to themselves reading or talking to each other, they went to bed around ten, Olive in the bottom bunk Dean in the top. Dean woke to the sounds of small whimpers coming from the bottom bunk, he knew his sister was probably having a nightmare, so he climbed down to check on her.  
   
"Olive wake up!" Dean said  
   
"What!?" She said rubbing her face  
   
"You're bleeding!" Dean said, sounding alarmed.  
   
"Crap, are they bigger!?" She asked almost crying  
   
"Not much, just a little it will be ok!" Dean said,  
   
"What's going on?!" James asked sleepily from the other side of the room.  
   
"Nothing goes back to sleep, sorry we woke you!" Dean said hastily, as he helped Olive up out of bed.  
   
"Let's go to the bathroom!" Dean said, taking her hand.  
   
"I don't wanna go out there, please don't make me!" Olive said crying, her horns were already painful and she didn't want to add more fuel to the gossip about her.  
"Alright wait here, I'm gonna get a bowl of warm water so we can clean them up ok," Dean said softly. She nodded, "Does it hurt?"  
   
"Yeah, awful this time!" Olive said, wiping the tears from her face in frustration.  
   
"I can help with that!" James spoke up again from his and Castiel's side of the room.  
   
"It's ok!" Olive said. James seemed very lovely, but angel magic wasn't something she had much experience with, and she didn't want to make it worse.  
   
"I really can help you," James said, sitting upon his bed.   
   
"It's ok, really thank you, but they aren't done yet!" Olive said  
   
"If you want my help, please tell me," James said kindly.  
   
"Dad. I don't know, I had to wake her up," Dean said on the phone.  
   
"Here, it's, dad!" He said handing Olive the phone  
   
"Hi Dad"  
   
"My sweet, are you ok?"  
   
"No! It hurts really bad."  
   
"I gave Dean a list of herbs the school should have to help with the pain."  
   
"Thanks, Dad"  
   
"I love you, kid!"  
   
"I love you too, bye, Dad!"  
   
She hung up and handed the phone back to Dean, Olive winced as he went to touch her horns.  
"I didn't even touch you yet," He said in surprise.  
   
"I know, I know, sorry it's just that it hurts! You have something forcing its way out of your forehead" She said, Dean smiled at her sadly and then carefully went about cleaning around her horns. Then he wiped the blood and tears from her face.  
   
"I'll get the herbs later, it's not open yet," Dean said  
   
"Thanks, Dean! Will, you lay with me?" She asked  
"Yeah get in the bed!" Dean said Olive laid down and Dean cuddled next to her.

 

 

 


	2. Chapter 2

Olive woke a few hours later to discover Dean was already gone and so were the twins, she got up and looked in the mirror, her horns were only a little bit bigger but they were still very tender.

 

“Ow!” She said when she poked at the newly cracked skin on her forehead.

 

“Good you’re awake, you have to go to the healer” Dean said coming in through the door.

 

“Let me get changed” She said looking around for something to wear.

 

“Are you ok?” Dean asked, turning away so that Olive could get changed in privacy.

 

“Not really. I mean I knew they would get bigger but it just hurts so badly” She said changing her clothes.

 

“Um, Dad asked me to see if you felt different, like more powerful?” Dean asked looking at her

 

“No. I don’t, don't worry I’m not gonna bend you to my will or anything” She said with laugh, he smiled and laughed a little.

 

“Hey by the way, will you be nicer to our roommates, I know you’re not an angel fan but they seem nice not like some of the other ones” Olive asked

 

“Fine, but only for you. They have really pretty wings, I know we aren’t supposed to look but...” Dean admitted in a whisper

 

“I know” She whispered back.

 

Together they went to the healers office, which was a large room filled with shelves, each shelf was lined with jars of liquids, herbs, eyeballs and some kind of preserved animal neither of them had seen before, Olive glanced at Dean this place wasn't very clean there was dust and cobwebs surrounding everything, it creeped Olive out but she needed the herbs for her pain so she took a deep breath and followed Dean further in to the room.

 

“Hello, I’m Alex the healer” Said a short demon with sleek black wings and a tail peeking out from under her tattered dark blue robes.

 

“I’m Olive” She said

“Your brother tells me you’re in some pain with your horns?” She said looking at her in a inquizitive way

 

“My horns grew overnight and it can be painful, my Dad gave Dean a list of herbs for me to take though” Olive said looking at Dean, the healer reaches up and Olive grabbed her wrist to stop her from touching her horns.

 

“Don’t” She said with a warning tone.

 

“Apologies miss”  Said Alex looking surprised. “I’ve never seen a horned demon” She said

 

“Don’t touch them, it's like touching my tail!” Olive said as her tail snakes up and rubbed against her face, she patted her tail.  

 

“Here are your herbs, please come back if you’re in anymore discomfort!”

 

“Thank you” Said Olive taking the bagand instructions and following Dean out of the door.

 

“So the party tonight…” Dean said

 

“What about it?” Olive asked slightly annoyed

“I just wanna make sure you’ll be ok?” Dean said

 

“You just wanna make sure I won’t summon you while you’re making out with some demon!” She said in an amused tone.

 

“You don’t have the best timing” Dean laughed

“Ok mister-I-summoned-my-sister-to-the-police-station and not just the police station but inside your cell” Olive said teasing him about the incident that caused their father to send them to boarding school.

 

“Fair point” Dean said opening the door to their room.

 

Castiel and James still weren’t back by the time Dean and Olive returned from the healer, so the room was empty when they arrived.

 

“I hope we didn’t freak them out last night!” Olive said

 

“Hey Olive!” Said Michael from behind Dean

 

“Hey!” She said shyly

 

“This is Dean!” She said introducing her brother and trying to take some of the focus off of herself.

“Nice to meet you, you’re still coming tonight, right?” Michael asked seemingly worried she may have changed her mind.

 

“Yeah, we will be there, it’s at your room right?” Olive asked

 

“Yeah. See ya then” Michael said walking backwards with a small wave, almost walking into another demon.

 

“Dean this is a paste, mom always gave me the ones to eat” Olive said looking at what the healers had given her for her pain and feeling annoyed that it wasn't what her mom gave her. “Are you sure this is right?” Olive asked

 

“Yeah O, that’s what Dad said would work” Dean said “I’ll make it!” He added taking the bag of herbs, about five minutes later it was ready. “Come here, it says leave it on for an hour and then wipe off!” Dean said reading the instructions on the bag.

 

“Please can you just call Dad to make sure it’s alright?” Olive said feeling wary of putting something on her horns that she wasn’t familiar with.

 

“Do you trust me?” Dean asked

“Always!” Olive answered, he lifted his hand but she pulled away before he could touch her, he sighed.

 

“They just hurt really bad” she whined “I do trust you, but I want to be sure”

 

“I’ll be gentle” Dean said and Olive just sighed and nodded allowing him to begin spreading the paste on the base of her horns. The door opened and Castiel and James came in.

 

“Should we leave?” James asked like he was interrupting something private.

 

“Stay, you’re fine!” Olive said they shut the door.

 

“So sorry about last night, they grow slowly and...”

 

Castiel put his hand up “You don’t have to explain it's ok, we share a room things are going to happen!” He said Olive smiled.

 

“We are going to a party tonight so we may come in late, I’d invite you but they said demons only sorry” She said

 

“It’s fine!” They said in unison, sounding a bit disappointed.

 

“Is it supposed to itch” Olive asked pulling her head away from Dean when she felt the itchy sensation on her forehead.

“I don’t know O. I don’t have horns” Dean said

 

“I’m aware” Olive said snapping at her brother

 

“It’s time to wipe it off” Dean said grabbing the wet washcloth.

 

“I’m sorry I snapped” Olive said

 

“O, it’s fine I know they hurt and if I could take that from you I would” Dean said “Now let’s go get something to eat I’m starving” Dean said holding out his hand.

 

James and Castiel watched them as they left the room,

 

“I wish she’d let me help” James said Castiel sighed

 

“Is it because you want to help or because you think she’s hot” He asked

 

“Really?” James asked with a roll of his eyes Castiel shrugged.

 

“I mean they both are, I love their wings they are so pretty”

 

“You mean Dean has pretty wings and a strong tail everything you’d look for in a demon” James teased

 

“Shut up” Said Castiel

 

“It doesn’t matter anyways he doesn’t like angels” Castiel said putting his head down.

  


They left to go see their brother who happened to be the angels studies teacher, they knocked on his door, see what he knew about horned demons and to check-in they had seen their older brother in a while, with him being away teaching at the school

 

“Brothers, how's today going?” Gabriel asked excited to see his little brothers

 

“What do you know about horned demons?” James asked

 

“Why do you ask? Jimbo” Gabriel asked

 

“One of our roommates, she’s got horns” he said

 

“You guys are roommates with the green eyed demons?” Gabriel asked and started laughing the stories of Dean and Olive were the stuff of legend, Dean sometimes enjoyed getting Olive to use her powers.

“I have heard rumors about those two, can they really summon each other?” Gabriel asked

 

“Yes!” They answered and Gabriel seemed impressed.

 

“I don’t know much, other then the horns come from the mother's side it just depends on what kind of horned demon she is” Gabriel said

 

“The really shy introverted kind” Castiel said

 

“Wait, did you say shy?” He asked sounding surprised.

 

“Yeah, why? She actually really nice for a demon” Castiel said

 

“That’s different, I’ll look into it more. Hendrickson is going to announce this later but I’ll give my baby bros a heads up you’ll be paired with a roommate and you’ll attend all your classes together, seeing as how no one can seem to get along yet” Gabriel said

 

“I hope I get Dean” Castiel said out loud without thinking, his brothers looked at him. “What?” He said, they shook their heads. Cas really wanted to get to know Dean he seemed nice for a demon, he cared deeply for his sister and maybe, just maybe he could change Dean's mind about angels.

 

Olive was waiting in line for her food, when she heard yet more muttering about her and her brother.

 

“I heard they can summon each other at will and that’s why she got in trouble he summoned  her” Olive heard in a whispered behind her

 

“What is wrong with you demons? Dean and I got in trouble and yes we can summon each other at will it’s a twin thing. Yes, I have horns I got them from my mother, so just stop talking about us we aren’t a novelty, we aren’t special, we are just demons.” Olive said storming off

 

“That was rude!” The demon that had been whispering behind Olive’s back said

 

“No what’s rude is talking about someone behind their back!” Dean said walking up to get his own food, then he turned away and followed after his sister.

 

“O, you ok?” Dean asked sitting next to her at the table.

 

“Yeah just annoyed” Olive said, she’ll never really understand what makes them so interesting that people need to talk about them, like none of them ever got into trouble before.

 

“Can I sit with you?”

 

“Yeah sure” Dean said looking up at the girl in front of him who’d spoken.

 

“I’m Charlie”

 

“Olive and this is Dean” Olive said

 

“Dean and I met already, are you going to Michaels party?” She asked

 

“Yes we are” Dean said

 

“Are you going?” Olive asked

 

“No not really my thing, I do movie nights once a week in my room Friday nights you guys should come sometime if you’re interested” She said Olive looked at Dean

 

“Thanks, we’ll think about it” Dean said

 

“You’ve got a little” Charlie said quietly, she pointed and Olive raised her hand to her head where she cool feel something trickling down her skin. She had a trail of blood rolling down her forehead from her horns.

 

“Come on” Dean said taking her hand and leading her back to their room where he could help clean her up.

 

“I’m sorry” Olive said on the verge of tears. “I thought they were done” She added wiping the blood away with her sleeve.

 

“Come here I got it” Dean said helping her wipe the blood “How's the pain?” He asked her.

 

“Horrible, and they are still itching too” She said miserably

 

“You know, I always wanted horns” Dean said trying to reassure her.

 

“I know, I always hoped you’d have them too but in our family it’s a female thing” Olive said she stroked her brothers cheek with her tail, he smirked.

 

“You know she’s got a mind of her own” Olive said grabbing her tail

 

“I know, I love you sis”

 

“Love you too” They wrapped their tails together.

  


They stayed in their room the rest of the day, Olive napped for while seemingly exhausted from the pain in her horns, then Dean woke her when it was time they headed down for dinner.

 

After dinner the headmaster made an announcement...

“As you all know this school is about including everyone and since some of you still seem to be having trouble with that you will now not only room with your roommates you will attend the same classes, you all have been carefully paired so no one’s classes have changed, I need the Novak’s and the Winchester’s to follow me to my office! Everyone else you are dismissed!” He said

 

“Did we do something?” Olive asked Dean who shrugged.

 

“You aren’t in trouble!” He said everyone let out a sigh of relief

 

“You are actually one of only room that hasn’t had any problems, so the reason I called you in here was because I know you room together but you all happen to already have all you classes together,  Castiel you’ll be paired with Dean and James you’ll be paired with Olive….” he said looking at her

 

“You’re staring!” She said annoyed

 

“Sorry” He cleared his throat “I’ve never….”

 

“Seen a horned demon before I know” She said her tail swished with annoyance, she was getting so sick of people saying that.

 

Dean's tail grabbed hers trying to calm her

 

“Are you ok?” He asked

 

“No my head hurts!” She said bothered by the fact that everytime he asks she gives him the same answer, like it was going to change

 

“I really wish you’d let me help!” James said

 

“Do you have to touch them?” She asked

 

“I won’t, if that's what you want but it would work better if I was able to touch you” James said

 

“It’s just that my horns are very sensitive to touch it’s like touching my tail” She said putting her head down.

 

“I won’t touch them then, I promise, I just want to ease the pain” James said

 

“Ok” Olive said with a sniff

“This is why we opened this school, getting along, helping each other” Hendrickson said excited to see the children of both leading families showing that they could get along and help each other.

 

“Do I have to do anything?” Olive asked

 

“No just stay there” James said standing in front of her he reached towards her head but she moved.

 

“Hold still O, close your eyes!” Dean said holding her hand. Olive felt a warm feeling buzzing through her horns and then nothing, no warmth and even better, no pain.

 

“Wow that’s it?” Olive asked

 

“That’s it!” James said

 

“Thank you James!” She said hugging him

 

“I’m sorry I shouldn’t have done that” She said backing up, she didn't want to overstep or offended him

 

“It’s no problem. Come on Cas!” James said leaving the office.

 

“She hugged you!” Cas said as they left the office

 

“I was there!” James said trying to hide his smile.

 

“That was really nice of you Jimmy, to not touch her even though it would have worked better!” Castiel said Jimmy nodded and opened the door to their room,

 

“All the other demons and the angels look at her and all they see are her horns, it clearly makes her uncomfortable and I don’t understand why other demons at least… aren’t more sensitive towards her… She is more than just a ‘horned demon’” Said Jimmy

 

“Do you really think so?” Olive asked standing in the doorway

 

“Uh you weren't supposed to hear that” Jimmy said embrassassed turning beet red, fidgeting with the hem of his shirt

 

“Well, I did hear it… Thank you” Olive said

 

“We’ve always liked demons but they haven’t always liked us and you were nice from the beginning and I just…”

 

“It’s ok I’ll just pretend I didn’t hear it, you don't have to explain” Olive said giving him a soft smile

“Ok” Jimmy said.

 

Later that evening Dean and Olive headed to Michael's room for the party they were invited to, Dean was worried about his sister, knowing parties were not really her thing but proud that she was stepping out of her comfort zone.

 

“Little sister are you ready to party?” Dean asked

 

“You're like an hour older than me and yes actually I am, my head doesn’t hurt for once” Olive said kind of excited about this party

 

“Alright sis ground rules, if anything makes you uncomfortable tell me, we will leave, don’t take drinks from people, and last but not least have fun!” Dean said want to make if clear that even if he was having a good time he would leave if she wasn't.

 

Olive smiled as they entered Michaels room, the music was low. There was Michael, Lisa and few other demons

 

“Are we early?” Dean asked looking around noticing only a few demons in the room

 

“No right on time” Michael said

 

“Thought you said this was a party?” Olive said

 

“It is” Michael said

 

Dean and Olive gave each other a look, Olive was still confused by a lack of demons invited or that showed up especially if this was supposed to be a party and everyone was talking about it at lunch.

 

“Dean come sit!” Lisa said patting the floor next to her smiling

 

“Olive come sit by me!” Michael said

 

“Here’s a drink” Michael added handing her a cup, she looked at Dean

 

“O doesn’t drink, I’ll take it!” Dean said

 

“Ok” Michael said handing it to Dean

 

“Hi I’m Benny” A big burly demon said with a thick southern accent

 

“Olive”

“Dean” They said respectively

 

“So how are your angels?” Benny asked

 

“Really nice actually” Olive said

 

“Yeah one helped O, with her pain” Dean said

 

“What pain?” Michael asked curious as to what they were talking about

 

“Um my horns grow slowly but when they do it hurts and the skin bleeds” She said looking down

 

“Why didn’t you just go to the healer?” Lisa asked

 

“I did, it didn’t help” Olive said

 

“Did it touch you?” She asked   

 

“No, _he_ was very respectful” Olive said her tail coiling up her arm

 

“Still I wouldn’t have it touch me, they are so self righteous” Lisa said shivering like she was shaking off a bad feeling

 

“Dean, do you wanna come back to my room?” Lisa asked snaking her tail around his arm,

 

“Um not right now!” Dean said clearly uncomfortable with her actions

 

“Are you a succubus?” Olive asked

 

“Yes I am!” Lisa said Olive raised an eyebrow at Dean, sex demons had a way with making the person they had their sights set on jump in bed with them without thinking first.

 

“So anyways what’s your name!?” Dean asked the demon sitting next to Benny

 

“This here is Andrea, she’s mute” Benny said the little demon smiled and waved. Olives tail gave a small wave, Andrea smiled.

 

They all talked about their classes and the angels they roomed with Benny didn't seem to mind his but Michael and Lisa seemed to hate theirs.

 

After a while, Dean went to Lisa’s room with her, Benny and Andrea took off too leaving Michael and Olive alone, they were still sitting on the floor in Michaels room

 

“Um so, do you have a demon at home?” Michael asked

“Ha that’s funny!” Olive said lack of amusement in her voice

 

“A beautiful demon like you” Michael said sweetly

 

“Yeah right, I’m the weirdo with the horns, demons are scared of me” She said sitting next to Michael,

 

“What about you?”

 

“No, actually” Michael said scooting closer to Olive

 

“Does your tail always do that?” Michael asked as her tail rubbed her cheek and wrapped around her neck like a necklace

 

“Yeah sometimes she has a mind of her own” Olive said

 

“Your tail does what it wants?” Michael asked

 

“Sometimes, But I can control it too” She said rubbing the back of her neck

 

“I’m sorry, we shouldn’t talk about your tail” Michael said he leaned in, inches away from her

 

“Can I touch your horns?” He asked

 

“No!” Olive said offended at such a statement, she stood trying to get some distance between them,

 

“That’s worse than touching my tail, you’re not my mate or my family” Olive said trying to move passed Michael he blocked the way  

 

“Come on you let the angel!” Michael said moving so she couldn't get past

 

“No. I didn’t, he didn’t have to touch them to heal them” Olive said. Michael grabbed her hands in one of his pinning them to together in front of her

 

“Come on let me, I’ll be your mate” Michael said reaching up to touch her horn, Olive started to shake, she summoned Dean back to the room

 

“What the fuck are you doing!?” Dean yelled grabbing Michael and shoving him away from Olive

 

“She’s…. I’m sorry”  He said letting go Olive ran out

 

“Just leave her alone, she's not a plaything she is a very special demon and you’re lucky all she did was summoned me!” Dean said leaving to find his sister.

Olive was crying when she made it back to her room.

 

“Olive what’s wrong?” Jimmy asked

“He tried to touch….” Olive said sobbing not able to get the word out

 

“Do you want a hug?” Jimmy asked “I won’t touch your horns” She nodded he wrapped his arms around her holding her tight, he felt horrible that someone would be so mean to Olive, she was so nice.

 

“It was terrible!” She said through sniffs

 

“O!” Dean said Jimmy let go and moved back to his side of the room, so Dean could take care of his sister.

 

“I’m so sorry. I shouldn’t have left you alone with him!” Dean said holding Olive, feel extremely guilty for not being there to protect her from that asshole.

 

“I didn’t think he would…” Olive said crying into Dean's shoulder “Every damn time”

Dean let go she could climb into her bed

 

“It’ll be ok O, you’ll find someone who will like you for you and not just your horns” Dean said

 

“I’m gonna go to sleep now” She said sounding sad “Sorry for pulling you away from Lisa”

 

“It’s ok, get some sleep, goodnight” He said. It took a long time for Olive to fall asleep and the sound of  soft snores to come from her bunk.

 

“Hey James” Dean said

 

“Yes?” He questioned putting his book down and looking at Dean.

 

“Um thanks for, ya know, being so nice to O, she’s sweet, almost too sweet for a demon” Dean said, he knew the angel had made a good impression on Olive and he wanted to make sure that Jimmy knew how much Dean appreciated someone being there for his sister.

 

“She been nice to us. I don’t like that other people are so insensitive towards her. It can’t feel very nice to be singled out for something she has no control over. ” Jimmy said.

  
  
  


 

 

 


	3. Chapter 3

**3**

 

Monday morning was the start of classes, everyone was paired with their partners. Castiel was nervous, Dean had barley said five words to him since they had arrived and now they were expected to not only to room together but also attended classes together. James and Cas had already headed down to the dining hall for breakfast when Dean and Olive woke up.  Dean and Olive took a little longer to get ready and start the day as Dean needed to mix the herbs that kept Olives powers in check.

 

“O, are you sure you’re gonna be ok?” Dean asked while standing in the breakfast line, knowing Olive had a tendency to get nervous and summon him at random times.

 

“Yes dearest brother. I will be fine, will you?” She asked sarcastically, Feeling annoyed by his questions before she had had chance to have some coffee.

 

“Hey, Olive can talk to you?” Michael asked timidly feeling horrible about trying to molest Olive and wanted to make things right with her again. 

 

“No!” She said walking away, heading to a nearby table, she was not in the mood to listen to some half assed apology. She took a seat next to James hoping Michaels hate of angels would stop him from following her.

 

“Come on, Olive please I made a mistake” Michael said, clearly he wasn’t ready to let this go just yet.

 

“No, a mistake is calling me the wrong name! You tried to violate me!” Olive said in a hushed voice not wanting to draw too much attention to them.“Just go away, ow shit!” She said grabbing her head, in pain. 

 

“O, Olive look at me” Dean said pushing Michael out of the way.

 

“It hurts!” She said grasping  her head tighter.

 

“I know, I know” Dean said hugging his sister.

 

“Miss Winchester, is everything alright?” The headmaster asked coming over to see what the commotion was. 

 

“It’s her horns, it will take a few days for it to stop” Dean said offering an explanation as to why his sister was doubled over in pain.

 

“Take your sister back to her room. She can start when the pain goes away, James can you bring her classwork help make sure she doesn’t fall behind?” He asked 

 

“Of course, I’ll take notes for the both of us” He said more than happy to help Olive.

 

“Thank you” She said getting up, Dean wrapped his arm and his wings protectively around his sister, trying to shield her from all the staring and headed their towards their room. 

 

Once back in their room Dean got Olive helped to get her comfy trying to help as much as he could with her pain, he hated that he couldn't take her physical pain away.

 

“Alright, I will be back at lunch to check on you” Dean said 

 

“I’ll be fine, be nice to Cas, ok?” Olive said 

 

“Just for you” Dean said smiling, she smiled back and groaned holding her hand to her horns.

 

“Try to sleep for a bit, you know it helps” Dean said taking one last look at his sister before reluctantly leaving. 

 

“Is she Ok?” Michael asked as Dean walked out of the room, he must have followed them out of the dining hall and was waiting outside their door.  

 

“Yeah she’ll be fine, just leave her alone!” Dean said wings spread showing his height, in a  display of dominance.

 

“I was an asshole. I want to apologize, I shouldn’t have done what I did” Michael said sincerely.

 

“You mean hold her hands down while you fondled her horns?” Dean said loudly 

Michael nodded ashamed of his behaviour, he didn't meant to hurt Olive he was just use to getting what he wanted.

 

“You touch my sister again and I’ll kick your ass” Dean said walking away, Castiel was waiting for Dean outside their first class 

 

“You didn’t have to wait for me” Dean said 

 

“I know but Olive is a friend I want to make sure she was ok” Cas said 

 

“Oh, Um... yeah it just takes a few days for everything to settle the skin is really tender and the new growth needs to harden” Dean said 

 

Jimmy headed to class by himself hoping Olive was ok, he really hoped healing her would have helped, he would have to ask Gabriel if he knew why it didn't work or at least only worked for a little while. 

 

“Welcome to Angels studies” Gabriel said with a huge smile “You guys can call me Gabriel, I'm not really big on formality” 

 

“Now it seems we are missing Olive, uh James where’s your partner?” Gabriel asked calling out his brother partly concerned, partly  he just wanted to embarrass his brother.

 

“She’s having some issues today the headmaster should have let you know” James said Gabriel nodded 

 

“See me after, I’ll give you her class work” Gabriel said.

 

After class James stayed behind to gather up the notes and class work for Olive.

 

“Now really, what’s up with her?” Gabriel asked 

 

“I don’t know, I thought I healed her, I guess it’s her horns, they grew a bit and she was in so much pain. Do you know why it didn't work?” James said

 

“No I don't. Do you have a crush on her? You can tell me no judgement here” Gabriel asked almost teasing

 

“I might, I’ve only known her for a few days, but she’s really, really nice” James said

 

“For a demon?” Gabriel said 

 

“No, it’s genuine, she walked in on Cas and I getting dressed, she was so embarrassed she summoned her brother by accident and she does this thing with her tail when she embarrassed, she rubs her cheek with it and then gets more embarrassed and she grabs it” James said a little embarrassed that he knew that much about her already. 

 

“So, you do have a crush, little brother. I did some research, her tail can do things on it's own that’s why it rubs her cheek when she embarrassed, I don’t know what kind of demon she is but I’m sure she powerful, Dean has to be too since they are twins. You should get to class and good for you not to share Olives personal business” Gabriel said. 

 

Cas and Dean went their angels studies class, Cas stopped them outside the door.

 

“Um my older brother is the teacher” Cas said 

 

“Ok” Dean said heading inside and taking his seat.

 

“Welcome it’s good to see everyone here, Dean send my regards to you sister we missed her today” Gabriel said 

 

“I will, I’m sorry” He said and disappeared.

 

“Where did he go?” Gabriel asked looking at the spot where Dean had been sitting. 

 

“Olive must be upset or something and summoned him” Cas said Gabriel nodded. 

 

Dean appeared in his room. 

 

“O?” He asked, she was crying in her sleep. 

 

“Shit! Olive wake up” Dean said shaking her. The room started to shake violently she never had control when she was asleep, but this was bad.

 

“Damnit O” Dean yelled

 

“What!?” She said breathing heavy, the shaking stopped when she woke. 

 

“You were having a bad dream, you summoned me” Dean said feeling bad that there was nothing he could do to stop the nightmares she had of their mother, holding his sister was all he could to help her.

 

“Dean, I’m so sorry, I hate that I can’t control it” Olive said 

 

“Just breath it’s ok” Dean said rocking her a bit, Cas came in the room looking concerned.

 

“Give me a minute” Dean said Cas nodded and left the room,

 

“I’m gonna go back to class, give Dad a call” Dean said making sure Olive was settled before heading back to class

 

“Sorry, Gabriel sent me” Cas said explaining why he was there he didn't want to say he was worried about the both of them. Dean was at least talking to him more and he didn't want to ruin that.

 

“It’s fine, she was just having a nightmare” Dean said nonchalantly like it explained everything as they walked back to class. 

 

Olive took Dean's advice and called their Dad, hoping he could offer some advice 

 

“Hey Dad”

 

“Shouldn’t you be in class little demon?” 

 

“The Headmasters giving me a couple of days cos my horns”

 

“I’m sorry, the herbs didn’t work?”

 

“No and James tried to heal them it worked for a while but they grew a little more so just undid what he did”

 

“Whos James?”

 

“One of the angels we are rooming with”

 

“You ingested them right?”

 

“No she gave me the ones for the paste”

 

“I’m calling and make sure you get the right herbs so you can go to class”

 

“Thanks Dad”

 

“Alright, I love you”

 

“Love you too”

 

Her Dad called her back letting her know that he had talked to the healer and she should receive the right pain herbs to take with ones she was already on she headed back to the healers, 

 

“Hello” Said the healer as she arrived. 

 

“My Dad called” Olive said “John Winchester”

“Oh yes. Your father cares deeply for you” Said the healer 

 

“I am very aware” Olive said feeling annoyed at the idea that anyone would think that her father wouldn’t care for her. Why would that be a surprise? 

 

“I’m sorry about the other day, I didn’t mean to offended you” She said

 

“It’s ok you didn’t know” Olive said knowing that most people didn't mean to be offensive they just were curious. 

 

“Here are your herbs, and they shouldn’t interact with others you’ve used” She said handing them to Olive. 

 

“Thank you” Olive said leaving. 

 

Dean, Cas and Jimmy went to the room to get for lunch Olive she was sitting in the middle of the room staring her tail waving in front of her 

 

“Hey O, you ok!?” Dean asked frowning at her. 

 

“Hi Dean” She said sounding distant. He spotted the herbs sitting on the desk.

 

“She’s stoned” Dean said with a laugh, offering an explanation as to why she was acting so weird to the angels stood behind him.

 

Cas and James looked at each other, 

 

“Sister, how much of these did you take?” He asked concerned at seeing how out of it she was, she always waited for him to mix things for her, he was better at it, herbology was his strong suit not hers.

 

“I don’t know” She said looking at him as though not really seeing him,

 

“It still hurts, Mom always made it better” She said tears in her eyes 

 

“I know” He said kissing her forehead. 

 

“You should eat something” Dean said helping her up her tail tapped Dean and he looked down at it. 

 

“She’s alright” He said, her tail seemed to understand and settled around her arm with the tip resting over her shoulder. 

 

“Hi guys” She said smiling. Having only just noticed that James and Cas were waiting.

 

“Hi” they said in unison

 

“Dean they are really cute” She whispered... really loudly.

 

Dean laughed at the fact that she thought that she was whispering but they still heard her, Jimmy and Cas hid their smiles not wanting to embarrass her, Dean lead her to the dining hall and sat her down, he went and got food for the both of them but not really wanting to leave her alone know full well what the pain herbs do to his sister when she took too much

 

“Stay! Make sure she stays!” He said to her tail, hoping that it would listen to him and keep her safe for five mins, it unwrapped from around her arm and wrapped around the back of the chair so if she got up she couldn’t go anywhere. 

 

“I know we aren’t really supposed to ask but…” Cas stammered nervously. Dean looked around, there weren’t many people yet.

 

“She’s unique, her tail can do somethings on its own, I’m not sure how it works. I control mine, it does what I want . Hers always finds someway to comfort her and gets concerned when she’s not right” Dean explained and Cas nodded

 

“We shouldn’t be talking about this!” Dean said suddenly uncomfortable, talking about his sister without her around 

 

“I’m sorry I shouldn’t have bought it up!” Cas said

 

“Where did she go?” Dean said going back to the table looking around. 

 

Michael saw Olive sitting alone, he thought it was as his opportunity to apologize to her, he asked her to step away from the table so they could talk  

 

“Olive, I really am sorry” He said, she smiled wickedly at him before she answered. 

 

“I don’t care” She said laughing a wicked laugh Michael had never heard, her eyes flashed black 

 

“I…” he coughed, he coughed more, then he was gripping his neck looking scared, he was choking. Olive backed up from him when he reached for her, he coughed up a small horn and gasped for air. Looking from the horn in his hand to Olive with fear in his eyes.

 

“Now you have your own” She turned and walked away smirking. 

 

Dean spotted Olive talking to Michael by the window not to far from where Dean had left her, and hurried over to see what was going on.

 

”O what did you do!?” Dean asked angry worried she hurt him unnecessarily. 

 

“Gave him what he wanted” She said like it was no big deal she just used her powers on another student.

 

“She did this?” Michael asked showing him the horn he coughed up covered in blood.

 

“Dude I told you to leave her alone” Dean said 

 

“How did she do that?” Michael asked startled. 

 

“I told you she’s special, just  _ please _ leave her alone” Dean said walking away. 

 

Olive was sitting next to Jimmy when Dean walked back to the table, her tail snaked around her neck like a necklace.

 

“O, you’re not yourself right now, what’s going on?” Dean asked kneeling next to her, making her look at him.

 

“I…. he tried to touch something that wasn’t his to touch, he tried to say he’d be my mate but a mate doesn’t do that, a mate respects you” She said.

 

“Olive… Just eat your food please” Dean said knowing that when the herbs wore off and she was back to her normal self she would feel horrible about what she just did.

 

“Ok Dean” She said almost robot like.

 

Jimmy and Cas just watched her, Jimmy leaned across the table and looked at Dean.

 

“Is she ok?” He asked concerned about how she was acting 

 

“She will be, once the herbs wear off, she just took too much, she should have waited for me” Dean said, Olives tail uncoiled from her neck and snaked around Jimmy’s wrist 

 

“Dean what do I do?” He asked looking slightly nervous. 

 

“Nothing, she’s not doing it her tails just checking you out is all” Dean said watching carefully as her tail uncoiled from his wrist and snakes around his arm like it does with Olive when she needs comfort or something that would be done with a mate.

 

“Oh... Jimmy I need you to move away from my sister, you didn’t do anything wrong just do it slowly!” Dean said knowing this was something only done with mates and not friends, Jimmy stood slowly her tail uncoiled from around his arm and back around Olives neck.

 

Olive continued to eat her food not noticing, that her tail was making the moves on Jimmy, Jimmy looked very concerned like he did something wrong. 

 

“I’ll explain when we get back to the room” Dean said “O, let’s go back to the room” 

 

“Ok, I’m tired now” She said slowly blinking her eyes turning black, back to green,she got up and followed her brother. 

 

Dean laid Olive down in bed she fell asleep quickly leaving Dean to explain her actions two very worried angels,

 

“I’m so sorry!” Dean said embarrassed for his sister to Jimmy 

 

“What was that!?” Cas asked 

 

“This is going to be so embarrassing for her!” Dean said rubbing his face 

 

“She must be attracted to you! That wasn’t her doing that she would never, I hate talking about her like this but you need to understand” Dean said taking a breath Jimmy and Cas waited. 

 

“What do you mean that wasn’t her, it’s her tail” Jimmy said 

 

“It’s hard to explain but for horned demons their tails can sometimes do things on their own like when we walked in, it was worried about her so it tapped me, she talks to it, it understands for the most part” Dean said, to the confused angels. 

 

“Ok have you ever noticed when she gets embarrassed it rubs her face, mines always around my leg when I'm walking and around my waist when I’m sitting hers is always somewhere where it can comfort her, subconsciously she was seeking comfort from you. I guess it’s part her liking you, part the healing you did, she is in pain” Dean said Jimmy nodded 

 

“I like her too! I think, I don’t really know her but I want to” Jimmy said looking at her, her tail laying across her chest 

 

“I’m sorry? You like her!” Dean said taken by surprise that Jimmy said he liked her back.

 

“Yeah she’s kind, and funny I want to know more, if, you know, that’s ok?” Jimmy said Dean looked at him 

 

“If you’re serious there’s stuff you’ll need to know about her” Dean said Jimmy nodded. 

 

They all headed back to their classes agreeing to let Dean explain every thing that happened while she was under the influence of the herbs

  
  


The student advisor knocked on the door checking to make sure Olive was alright after what happened in the dining hall

 

“Miss Winchester open the door!” 

 

“What?” Olive asked opening the door

 

“I’m Pamela, I came to check on you” She said, she was an angel of average height, with brown hair and brown eyes,she also had  rough way of speaking, sleek white wings 

 

“I’m fine, just tired” Olive Said “I’m gonna go back to sleep if there is nothing else” She said grumpily. She’d been woken up by banging on the door.

 

“About what happened at lunch, don’t do it again” Pamela warned 

 

“What happened at lunch?” Olive asked surprised 

 

“You don’t remember!?” Pamela asked Olive shook her head.“You made a boy cough up a small horn”  

 

“What!?” Olive said shocked that she used her powers on another student, her mom had always told her how seductive her powers were, how easy it was to use them to get what she wanted, so she had always tried not to use them.

 

“Don’t let it happen again” Pamela said walking away.

 

Jimmy made it to the room first Olive was pacing her tail flicking back and forth, 

 

“Hey how are you feeling?” Jimmy asked concerned and trying to avoid the death stare olive was giving him 

“What happened at lunch?” Olive asked 

 

“Maybe Dean should tell you, I have your assignments I’ll go over them with you” He said trying to change the subject, she stepped up to him 

 

“Tell me what I did” She said forcefully making Jimmy jump

 

“Olive” Dean scolded 

 

“I’m sorry, I’m not myself today” She said regretting getting in Jimmy's face.

 

“I have a few things to tell you, first you made Michael cough up a small horn which was really cool and not really something you would normally do and second your tail got frisky with Jimmy again not really your fault” Dean said 

 

“What did you do?” She scolded her tail. The tip hung down trying to show that it really didn't mean it, it only wanted to know him better “Time out” She added, her tail coiled itself around her leg the tip flat against her calf. Olive turned to James and said “Jimmy I’m so sorry, I never would have done that” 

 

“I know it’s ok, Dean explained as much as he could” Jimmy said smiling at her. She was always so cute when she was flustered.

 

Cas and Jimmy decided to go take a shower giving Dean and Olive a chance to talk about what happened without them being in the way.

 

“I am so mortified!” Olive said laying back on her bed throwing an arm over her eyes dramatically.

“Olive you should have waited for me to mix this for you” Dean said leaning over the side of his bunk.

 

“I’m tired of everyone treating me like a baby” She said sitting up so she could lean out and look at him.

 

“I know. I’m sorry, but you took too much, you were very stoned not that I don’t enjoy stoned you because she pretty great but you know it lowers your sense of right and wrong!” Dean said climbing down so they could talk better

 

“Should I apologize to Michael?” She asked

 

“No, that asshat deserved it! Very creative, by the way. His own horn the fondle whenever he wants” Dean said with a smile.

 

“I can’t believe my tail wrapped around itself Jimmy, that is so embarrassing” Olive said covering her face, that was what she was really worried about at the moment, not that she could have killed Michael by making a horn grow inside him, he was a pig and it was a pretty fitting punishment. 

 

“Do you like him? James I mean” Dean asked, he already knew the answer to this question they were twins after all he just wanted her to say it outloud.

“Maybe, would you be mad?” She answered want to make sure her brother was ok with the fact that she liked an angel.

 

“Nah sis, besides I think he likes you too” Dean said only wanting her to be happy.

 

“The other day I heard them talking and he said he sees more than just my horns, do you think Dad would be mad? He’s always going on about how we should get along but I don’t know how he’d feel about other stuff” She said not taking a breath between statements

 

“Don’t worry about Dad, just do what feel right for you!” Dean said. A little while later they headed to the dining hall for dinner, hoping everyone had forgotten what happened at lunch.

 

At dinner Charlie sat with them, she liked Dean and Olive, she also liked angels but her roommate wasn't as friendly.

 

“Hi, I’m Charlie” She introduced herself to the twins. 

 

“I’m Jimmy, he’s Castiel” James said 

 

“So, how are you liking school?” Charlie asked, she had been there a year already and liked being around everyone.

 

“It’s ok for our third day” Cas said

 

“You should eat with your own kind” Lisa directed at Castiel and James as she seated herself next to Dean. Charlie got up with a huff and left not wanting to deal with Lisa’s rudeness and hate of angels.

 

“You don’t have to leave” Dean said to Cas and Jimmy, annoyed that Lisa would just assume she could tell them what to do.

 

“So I heard you made Michael cough up a horn” Lisa said ignoring Dean and smiling at Olive.

 

“That’s what they tell me!” She said not really caring what Lisa thought.

 

“You don’t remember?” Lisa asked

 

“Not really, I got some stuff from the healer, I didn’t really know what I was doing, I was a little out of it” Olive said her tail crept out and settled on her shoulder “I’m alright!” She said to it quietly, it settled down on the table between her and Jimmy “Don’t even think about it!” She said grabbing her tail quickly, she so did not want a repeat of what had happened earlier.

 

“You talk to your tail?” Lisa asked like Olive was nuts for talking to something that didn't understand her. 

 

“It a bit sentient, it can do things on it’s own” Olive said 

 

“That is so cool, so it’s like a friend?” Lisa asked 

 

“Why are you asking me this?” Olive asked sharply 

 

“I’m not being mean, I'm curious” Lisa said offended 

 

“Sorry. I’m always the freak show, the one demons make fun of” Olive said pushing her food around with her fork. 

 

“I’m sorry, I may be a succubus but I’m not mean” Lisa said Olive nodded. 

 

After dinner they went back to their room to study, Jimmy had written notes for himself and Olive. 

 

“Wow! You have really nice handwriting” Olive said looking at the notes, admiring Jimmy's penmanship.

 

“The the angels studies teacher is your brother?” Olive asked reading the top of the syllabus, also surprised that they didn't say anything that their brother was a teacher at the school.

 

“Yes” Jimmy said 

 

“Am I in trouble?” Olive asked confused looking around and very worried.

 

“Why would you be in trouble?” Dean asked looking at his sister like she was crazy.

 

“I’m being summoned” She said and she was gone, she appeared in the headmasters office in front of his desk. 

 

“Oh good it worked” The headmaster said 

 

“Why did you just summon me? I could have been in the shower” Olive asked concerned that she was summoned instead of someone just coming to get her.

 

“My apologies, I won't do it again. I needed to speak with you and this seemed the fastest way to do that, I needed to speak with you, about what happened with Michael” He said 

 

“I didn’t mean to, I….” The headmaster put his hand up and Olive fell silent. 

 

“What he did to you” He said

 

“Oh, we went to hang out in his room Dean and I.He said it was a party, after a while I’m Dean went to hang out alone with Lisa and than the other demons left so Michael  and I were alone, he um asked to touch my horns” She said reaching up placing a protective hand over her horns“I said no that it was like touching my tail, he’s not family or a mate and than he said he would be my mate and held my hands together in one of his and I got scared and called for Dean” She finished

 

“Now I understand, very creative by the way, do you want us to do something with him, this won’t be tolerated” He said smirking at Olives creative punishment, after all he was an angel had nowhere near her amount of power

 

“No, I just want him to leave me alone, he apologized but it’s not like an accident, ya know?” She said he nodded

 

“As creative as your punishment was you can’t curse students, this is a warning. Next time you’ll get detention” He said Olive nodded 

 

“You’re dismissed” He said. 

 

Olive walked back to their room, relieved she wasn't in that much trouble and happy to know that if it ever happened again something would be done about it.

 

“O, what happened!?” Dean asked checking over his sister, making sure she was alright

 

“I’m ok it was the headmaster he just wanted to talk” Olive said smile 

 

“I may be in a bit of trouble for Michael but he did say if I did it again, I’d only get detention” She said.

 

“I finished the classwork, if you want to look at it” Jimmy said interrupting their conversation. 

 

“Thanks” She said with a big smile. 

 

The next morning Dean mixed the proper dosage of herbs for Olive and they went to breakfast. 

 

“Hey” Charlie said 

 

“Hey” Olive said loading her plate with food

 

“I have a question for you” Charlie said

 

“Is it about my horns?” Olive asked bluntly 

 

“No, it’s about Jimmy” Charlie said she chuckled slightly at Olives question. 

 

“What about him?” She asked feeling oddly defensive of James and slightly concerned that Charlie seemed to be interested in him. 

“I was just wondering if you liked him” Charlie said. Olive looked at her by the tone of her question it sounded like she didn’t like the idea of angels and demons being together.

 

“Oh! No I’m not…. I don’t hate angels. I just think you two would be cute together is all” She said back tracking 

 

“I guess kind of... he’s been very nice to me” Olive said with a small smile, thinking that really she had a giant crush on the angel but wasn't going to let anyone know in fear of it getting back to Jimmy and him not reciprocating her feelings.

 

“Your Dad is the head of the demon faction right?” Charlie asked

 

“Yes he is. The Midwest.” Olive said 

 

“That’s really cool, so um do you think he’d be ok like if you and Jimmy were to, ya know?” Charlie said 

 

“I don’t know. I think so he’s always going on and on about how we all aren't really that different” She said following Charlie to the table, her tail snaked up her arm and laid on her shoulder. 

 

“Can I ask?” Charlie said pointing to Olives tail.

 

“Well, it’s sentient kind of I mean I can control it like other demons but she’s got a mind of her own sometimes, she does as she pleases even tho it gets her in trouble” Olive said smiling 

 

“I’m sorry but that is so cool, I wish mine did that, I just have a plane old boring tail” Charlie said 

 

“What’s really cool?” Deans asked

“Nothing important just talking” Olive said her tail gave a small wave

 

“Don’t try to suck up to him, I’m still mad” Olive said her tail laid down

 

“That is so cool!” Charlie said smiling. 

 

Jimmy and Cas found Olive and Dean sitting with Charlie and took seats next to them, talking and eating before heading off to their classes.

 

“About Angel studies, our brother can be a bit of an ass, he spent some time as a trickster, thinks it's funny to play tricks and stuff. I'm sure he won't mess with you, I just want you to be prepared” Jimmy said as they walked to class 

 

“He’s not going to say anything about my horns is he?” Olive asked her only concern was her horns being pointed out by a teacher.

 

“No, I hope not!” Jimmy said as they walked in to door and took their seats, most of the demons sat together, Lisa was in the same class,

 

“Olive come sit we saved you a seat” She said waving her over Olive looked at Jimmy her tail grazed his hand just enough no one could see, but Jimmy felt it.

 

“It’s ok, go on” Jimmy said smiling to himself, happy to know that she felt the same way he did even though she hadn't said anything yet.

 

“Ok, let’s get started Olive nice of you to join us today” Gabriel’s said Olive blushed her tail wrapped protectively around her neck

 

“Behave” She whispered to her tail the last thing she needed was to be singled out because her tail was bored.

 

After class Gabriel called her over to his desk, wanting to get to know the demon that his baby brother was crushing on also a bit of his own curiosity about horned demons. 

 

“Olive, will you stick around please?” Gabriel asked “I just want to make sure you are ok!” He said noticing the concerned look on her face.

 

“Um yeah and I’m sorry I pulled Dean out of class the other day” She said putting her head down and blushing.

 

“You are very different aren’t you?” Gabriel said noticing she didn't carry the same bravado that the other demons had.

 

“I guess” She said blushing harder rubbing the back of her neck

 

“I see why my brother likes you” Gabriel said smiling. 

 

“Wait, what?” She said the statement taking her by surprise 

 

“Off to class!” Gabriel said not wanting to give too much away but give them the push they needed at the very least tell each other how they felt.

 

The rest of the day went smoothly. Olive stopped by their room to get more herbs that Dean had premixed for her. Some with pain killers, some without. They would help her control her powers, she took them and went to the dining hall, to find her brother.

 

“Olive come sit” Lisa called out but Olive pointed to another table where Dean was sitting with Charlie, Cas and Jimmy. Lisa gave her a disappointed look, Olive didn't really care, she didn't care to much for Lisa.

 

“What do you mean she brushed your hand?” Dean asked not believing his sister would do something so forward with her tail whilst not being affected by strong herbal medicine. 

 

“Like she wasn’t sure if it would hurt my feelings, if she didn’t sit with me”Jimmy said. He wasn't trying to say anything bad about Olive he just thought that Dean could give him some insight into how Olive was feeling about him. 

 

“It was quick, I don’t even think she noticed she did it” He added 

 

“In coming” Cas said spotting Olive walking up. He didn’t want her to think they were gossiping about her, even though they kind of were. 

 

“Hi guys” Olive said eyeing them 

 

“Hey” They said at once 

 

“Something going on?” she asked

 

“No, but I do need to talk to you about something” Dean said 

 

“I’m kinda hungry can it wait?” She asked shoving food in her mouth to make a point.

 

“Yeah of course eat your food, I’ll see you later” Dean said, leaving the dining hall, to get to his next class, Cas right behind him.

  
  
  


“What’s with you and Lisa!?” Dean asked as they walked back to their room after classes were done for the day

 

“I don’t know she’s being nice but I assume it may just to get in your pants” She said Dean opened the door and followed Olive in

 

“Hey um so Jimmy said you brushed his hand with your tail today during class” Dean said not waiting any longer to bring it up 

 

“No I didn’t!” She said offended by the fact that he would think she would do such a thing with her tail, 

 

“What is with you?” She asked her tail, it swayed back and forth as if it were teasing her, telling her to make a move.

 

“O, if you like him it’s fine, I know he likes you” Dean said

 

“I don’t know Dean. There’s so much about angel culture I don’t know. I don’t want to offended him” She said making an excuse not to put her feelings out there and what if he was like all the others only interested in her horns and her as a demon.

 

“Talk to him, see where it goes” Dean said like it would make all her worries go away.

 

“You first, I see you staring at Cas” She said taking the focus off herself. 

 

“This is not about me” Dean said turning it back to her, he wasn't going to let her out of this conversation so easy.

 

“Whatever” Olive said ending the conversation. Dean would admit his feelings when he was ready and so, would she. 


	4. Chapter 4

**4**

 

Three months into school and Cas and Dean have an overnight field trip for their art class.

 

“Alright, Jimmy take care of my sister” Dean said patting him on the shoulder. Dean had been making more of a effort to get to know Jimmy and Cas better since Olive seemed to enjoy spending most of her time with them.

 

“I will always look out for her” Jimmy said with a soft smile, Olive blushed slightly embarrassed by his statement.

 

“Be a good demon while I'm gone and please, please do not summon me” Dean said 

 

“Go. I’ll be fine and I will do my best” Olive said hugging Dean who as much as he was excited about this trip, still did not want to leave his sister behind.“Text me” She said as they left, Dean and Cas waved goodbye.

 

Jimmy ate lunch with Olive both not really knowing what to say without their brothers there to buffer the conversation, it's not that they didn't like being with each other they just didn't know how to start a conversation they were alone together and not having a textbook or notes between them.

 

“I’m sorry. I’m not very good company” Olive said feeling like she should break the silence between them feeling bad that she was being quiet. 

 

“Olive, this is the first time we have been alone together” Jimmy said with a small laugh knowing she was just trying to get him to talk to her. 

 

“You are not wrong, I just hope I don’t accidentally summon, Dean” She said

 

“You’ll be ok, besides, you got me” He said with a smile, she turned her head and covered her smile before biting her lip, he blushed realizing what he had said.  

 

“Isn’t there like a lady angel you can flirt with?” Lisa asked annoyed that he was sitting with Olive. 

 

“Don’t be mean to him, he’s my friend” Said Olive tired of Lisas hate towards angels. 

 

“Anyways you’re coming to my room tonight” Lisa said like her and Olive were friends. 

 

“No I’m not” Olive said with a small laugh. 

 

“Yeah you are, Dean's away for the night, you can do what you want” She said adding a bit more force to it like it would change Olives mind. 

 

“He doesn’t control me, I can do as I please. I just prefer staying in my room” Olive said

 

“Ok, anyways I will see you after dinner” She said walking away. 

Olive and Jimmy headed back to their room after lunch passing by the angels and demons hanging out. 

 

“I don’t wanna hang out with her, I don't even really like her” Olive said as they headed back to their room to hang out.

 

“Then don’t go, there's nothing that says you have to hang out with her” Jimmy said walking back to the room.

 

“Hey, go find someone else to talk to” A demon said to Jimmy 

 

“Who are talking to?” Olive said stepping into the demons space

 

“Pretty demon like you shouldn’t be around scum like him” He said “I’m Cole” He had brown hair, ice blue eyes with small wings for a male, short tail and a cocky attitude.

 

“I don't care who you are or who you think you are” Olive said taking Jimmy’s hand and walking away. Cole grabbed her other hand. 

 

“Don’t touch me” Olive said eyes flashing black for a second before she regained control. 

 

“Let her go” Gabriel said as he came walking down the hallway. 

 

Cole let go, holding up his hands backing away down the hallway. 

 

“Come, in your room” Gabriel said ushering Olive and Jimmy along. 

 

“What was that about?” Gabriel asked concerned 

 

“I guess I’m fair game without Dean around” Olive said sitting in her bed annoyed by the fact that everyone thinks they can get away with treating her differently when Dean wasn't there.

 

“He didn’t like that we were talking” Jimmy said answering Gabriels question

 

“I actually came by because I have a question for you Olive, can you move things with your mind?” Gabriel asked 

 

“Sometimes, It doesn't always work sometimes it works a little to well” Olive said 

 

“Ok thanks. I’ll see you later” He said leaving excited that she could move things with her mind ment he was narrowing down the type of demon she was 

 

“Lock the door, please” Olive said moving her pillows around getting ready to lay down. 

 

“Why?” Jimmy asked

 

“Because Dean's not here and I wanna take a nap, don’t you?” She asked 

 

“I’m not tired” Jimmy said

 

“Ok, well I’m going to” She said laying down

 

“I’ll watch over you” Jimmy said 

 

“Thanks”’she said with a smile. 

Olive was tossing and turning mumbling small no’s, and muttering in her sleep. She was having another nightmare about when she found her mom.

 

“Olive wake up” Jimmy said shaking her like Dean told him to 

 

“Olive” He shouted 

 

“What?” She said startled, sitting up when Jimmy yelled her name.

 

“You were having a bad dream” Jimmy said 

 

“Sorry” She said laying back down

 

“Lay with me?” She asked Dean always cuddle with her after she had a nightmare and she just need a warm body next to her.

 

“I don’t think that’s appropriate” Jimmy said blushing but also a bit excited that she would ask him to lay down with her. 

 

“I’m sorry I offended you” She said turning away from him 

 

“No, I just really like you and I umm... you know what never mind I'll cuddle you” Jimmy said laying down. 

 

“Fold your wings so I don’t accidentally touch them and we all know my tail has a thing for you” Olive said blushing 

 

“It’s ok if you do” Jimmy said

 

“What?” She asked surprised that he would say it was ok, wings were important to angels you don't just let anyone touch them.

 

“I…. um… I  really like you a lot and I have never felt this way about anyone” He confessed. It felt nice to finally tell her, they just needed to be alone to get it out.

 

Olive sat up, looking at him making sure she heard him right. He really wanted her to touch his wing, and every part of her wanted to run her fingers down the silky black feathers.

 

“I like you too” she said smiling “Jimmy, are you sure it’s ok?” Olive asked hoping he was serious 

 

“Yeah as long as I say it’s fine” Jimmy said smiling,

 

“I know we aren’t supposed to stare but they are so pretty” Olive said 

 

“I like that you stare” Jimmy said. Olives tail rubbed his face.

 

“Sorry” She said grabbing her tail  “So um, how do I…?” 

Jimmy turned so his back was to her, “Oh don’t touch where they connect to my back that’s a whole different thing it's like a bonding spot I don't know how to explain it. When you touch the feathers make sure you go with they way they lay, not against” Jimmy said 

 

“Ok” Olive said reaching out and brushing her hand down his wings. 

 

“They are so soft” She said doing it again enjoying the silky feeling on her fingertips part of her was wondering how that would feel during sex she shook the thought from her brain. Jimmy moaned a bit.

 

“Am I hurting you?” She asked concerned.

 

“No, no it feels nice” He said with a smile to himself. She was so gentle touching him, not wanting hurt him and it was most definitely turning him on, as much as he tried to fight it, she stopped placing a hand on his shoulder turning him towards her.

 

“Since you let me touch your wings it’s only fair” She said taking his hand 

 

“Olive I…” Jimmy said nervously. He knew how much her horns meant to her and what touching them meant to a demon like her.

 

“It’s ok. I want you to beside my tail does wants it to…” she lifted his hand to her horn Jimmy swallowed 

 

“Are you sure?” He asked 

 

“Yes. I’m very sure, I like you” Olive said with a smile “Gently” He lightly touched her horns she smiled. 

 

“This is ok?” He asked gently brushing his fingertips from the base to the tip they weren’t very big just past her hairline 

 

“Yes it's nice” She said. Olive moaned quietly

 

“They are smoother than I thought they would be” Jimmy said, noticing how touching them was effecting Olive. 

 

“Your hands are really soft” She said closing her eyes leaning into his touch, knocking at the door interrupted them. Olive glared at the door.

 

“Always something” Olive said getting up and opening the door. 

 

“Change of plans we are hanging out here” Lisa said pushing her way into the room and looking around noticing Jimmy sitting on the bed she made a face at him. 

 

“Who’s we?” Olive asked 

 

“Me, Ruby, Meg” Said Lisa

 

“I don’t know who they are” Said Olive

 

“Don’t worry they are friends of mine” Lisa said Olive looked at Jimmy 

 

“I’ll go hang out with Gabriel tonight” Jimmy said sounding resigned. 

 

“Alright and you’re eating with us at dinner, No angels” Lisa said walking out

 

“I’m sorry, Jimmy” Olive said closing the door 

 

“Don’t worry about it, I know you like me and well Dean likes me sometimes and that’s all that matters to me” Jimmy said with a small smile. 

 

Olive looked up and him, he was so close to her and boy, did she wanna know what his lips felt like on hers more than anything in that moment she leaned in a pressed her lips to his. His breath hitched with surprise that she kissed him though it was not unwelcome. She stepped closer wrapping her arms around his feeling the softness of the short hairs on the back of his neck, his lips were soft against hers. Their lips moved gently together exploring each other. Her tongue brushed his bottom lip and he open his mouth, her tongue invaded his mouth, he tasted like the chocolate chip cookies he ate a lunch not an unenjoyable taste. He slid his hands around her waist pulling her closer to him, her tongue was slightly forked, not something Jimmy was expecting but really enjoyed, she turned the kiss in to small pecks before stopping all together,

 

“I enjoyed that” Jimmy said slightly out of breath 

 

“We should do that more” Olive said happy he enjoyed it as much as she did. 

 

Jimmy have her a smile and motioned to the bathroom before walking away, still smiling. 

She checked her phone to make sure she didn't miss anything, she had a text from Dean checking on her, she texted him back...

 

**Dean:  you ok**

 

**Olive: yeah sorry.some stuff I’ll tell you when you get back**

 

**Dean: did you let Jimmy touch your horns? :)**

 

**Olive: maybe ;)**

 

**Dean: you dirty demon :)**

 

**Olive: he let me touch his wings**

 

**Dean: well put a sock on the door**

 

**Olive: it’s not like that we just kissed**

 

**Dean: I’m happy for you! Really I am**

 

**Olive: thanks! :)**

 

Jimmy's phone chimed on his way back from the bathroom

 

**Cas: spill**

 

**Jimmy: who told you?**

 

**Cas: Dean text Olive they share emotions**

 

**Jimmy: I let her touch my wings**

 

**Cas: and?**

 

**Jimmy: I touched her horns and we kissed**

 

**Cas: nicely done**

 

**Jimmy: It was the best kiss**

 

**Cas: I am happy for you**

 

**Jimmy: thanks!**

 

Olive and Jimmy made their way to the dining hall trying not to draw too much attention to themselves but still stealing light touches, Olive sat across from Jimmy when they sat down at the table, her tail snaked under and rubbed against his leg.

 

“Behave” Olive said to her tail, it looked a bit sheepish and settled down around her waist seemingly annoyed that she stopped it from getting things started. 

 

“I don’t mind besides I kind of like it” Jimmy whispered Olive blushed “And I love when you do that” He said

 

“What blush?” Olive asked Jimmy nodded 

 

“I guess we will sit with you!” Lisa said. Olive looked up Lisa was flanked by two other demons both short brunettes with eyes, small black wings and tails wrapped around their legs.

 

“Leave” One of the demons said to Jimmy

 

“He is my friend! And doesn't have to go anywhere, if you don't like it you can leave” Olive said annoyed that they thought they could walk up and decided who eats with her and who doesn't.

 

“It’s ok Olive, I need to get to Gabriel’s anyways, I’ll see you in the morning” Jimmy said

 

“Bye!” She said giving a small wave with her tail he smiled, her tail laid on her shoulder and rubbed against her cheek to comfort her.

 

“I know” She said to it, knowing it too was sad that Jimmy was run off by Lisa and her friends. 

 

“Ya know, you don’t have to hang out with them” Lisa said

 

“Ya know you don't have to be rude about it, I want to hang out with Jimmy he is actually nice to me” Olive said poking her food with the fork wishing Jimmy would come back and she wasn't sitting with Lisa and her friends.

 

“I’m Meg” the demon sitting next to Lisa said 

 

“I'm Ruby” the demon who sat down next to Olive said. 

 

After dinner they all headed back to Olives room, much to her dismay she didn't wanna hang out with them. Another group of demons just using her for her powers or to make fun of her, it was different when it was her and Dean going around causing problems for the town but to have others do it just made her feel violated.

 

“Alright, now we have snacks and candles and a spirit board” Lisa said excited 

 

“I’m not messing with that” Olive said eyeing the spirit board her mother always said never mess with the dead, let it stay dead.

 

“It’s a games it’s not real” Meg said

 

“You keep telling yourself that, I'm still not messing with it” Olive said as the door opened and Jimmy walked in. 

 

“Hey!” Jimmy said

 

“I thought you were gone!” Ruby said rudely 

 

“I guess not and all my friends are on the trip so I get to hang out here in MY room” Jimmy said smiling at Olive, Olive smiled back grateful that whatever plans Jimmy had made, had fallen through and he was there with her. 

 

“Come sit!” Olive said patting the spot next to her.

 

“He’s not staying” Meg said 

 

“He is, this is his room and he’s my boyfriend so he can stay, I hope that's not a problem for anyone” Olive said looking at them 

 

“Olive.. are you sure we should tell everyone” Jimmy said smiling happily. She had just made them official.

 

“Yes, do we still have a problem?” Olive asked, looking around the room 

 

“Nope!” Meg said smiling to herself knowing how this was going to get under Lisa’s skin.

 

“Well, I see how it is. You’re against your own kind” Lisa said standing up offended that another demon would consider even touching an angel.

 

“I don’t have anything against demons. I just like angels and Jimmy in particular” Olive said Jimmy shifted closer to her, her tail wrapped around his waist happy he was close.

 

“Whatever, just no snogging in front of us” Lisa said  “I’m sure Dean will have a few things to say about it, when he gets back” she sat with smirk thinking that telling Dean would put a stop to Olive and Jimmy.

 

“Dean doesn’t care” Olive said back, annoyed that everyone thought that Dean was incharge of her, he is her brother not her father. Lisa texted Dean the second she got a chance complaining about Olive and Jimmy.

 

**Lisa: your sister!**

 

**Dean: what about her? Is she ok?**

 

**Lisa: dating an angel?**

 

**Dean: She can do what she wants, he makes her happy!**

 

**Lisa: it’s disgusting**

 

**Dean: just leave her alone**

 

**Lisa: fine**

 

**Dean: Good**

  
  


Jimmy let Cas know what was up before anyone else told him and he never heard the end of it,

 

**Jimmy: Olive and I are together**

 

**Cas: It’s about time**

 

**Jimmy: shut up!**

 

**Cas: one down**

 

**Jimmy: should be easier to get Dean on your side**

 

**Cas: at least he’s talking to me**

 

**Jimmy: see, that's an improvement**

 

Lisa, Meg and Ruby took off not to long after Lisa texted Dean. 

 

“I guess we made them uncomfortable, I’m sorry I just made a decision for the both of us. I didn’t even ask you” Olive said making sure the door shut all the way.  

 

“I’m happy you said it” Jimmy said with a smile, really excited they were officially a couple “I’m gonna go take a shower” 

 

“I’ll be here” Olive said. 

 

Jimmy gathered up his stuff for the shower and left giving Olive a kiss on the cheek. As he walked down the hall Cole yelled at him, he was half expecting everyone to know already but this was crazy.

 

“Hey!” Cole yelled at Jimmy 

 

“What!?” Jimmy said, all he wanted to do was go take a shower.

 

“Find one of your own kind!” He said Jimmy looked at him

 

“What color are Olives eyes?” Jimmy asked he wasn't going to let anyone tell him who he could be or not be with.

 

“What?” Cole asked other demons and angels gathered around. 

 

“Olive, I assume that’s who we are talking about?” Jimmy said

 

“Yeah, I am. She shouldn't be with the likes of you” Cole said 

 

“Two questions, first what color are her eyes?” Jimmy asked again 

 

“Brown!” Cole said

 

“Second what color are her horns?” He asked 

 

“Black!” Cole said 

 

“Her eyes are green jackass! And all of you wonder why she doesn’t want any of you” Jimmy said 

 

“What does that matter what color her eyes are?” Cole said like he was trying to prove some point, but clearly missing Jimmy's point in asking him these questions.

 

“It matters because all you see is her horns andher power, you know what I see? I see her beautiful green eyes, the way her cheeks flush pink when she’s embarrassed, the way she smiles so big it lights up the room. The way she laughs when she thinks something’s funny and  the passion she has when talks about something she loves! But none of you see that so leave her alone and leave me alone” Jimmy said walking away.

 

Olive paced her room, beginning to feel bored of being alone she gathered her own stuff to take a shower. When she walked into the shower room, an angel turned to see who’d come in and scowled at her. 

 

“Who do you think you are?” the angel asked 

 

“I’m sorry?” Olive asked confused on why she was being confronted by an angry angel. 

 

“James and you? A demon?” The angel asked

 

“Ok, well he likes me and I like him so... what’s the problem?” Olive asked very confused as to why she was being attacked by an angel she didn't even know, she’d known the demons wouldn’t be happy, but she had hoped that at least the angels wouldn’t have minded. 

 

“You! You’re the problem!” She said 

 

“I suggest you get away from me!” Olive said feeling herself getting angry. 

 

“Why demons don’t have many powers anymore, you’re just weak” She said pushing Olive back against the wall cleary this angel didn't know who she was messing with 

 

“Leave me alone” Olive said trying to move past the angel blocking her way before the angel could do anything she was blown backwards “I said leave me alone!” Olive said eyes flashing black and back to green before the angel noticed walking towards the shower stall. 

 

Olive showered and went back to the room, when she walked in Jimmy was trying to dry his wings. 

 

“Can I?” Olive asked watching him struggle. 

 

“Sure” Jimmy said admitting defeat and handing her his towel. 

 

“Come sit” Olive said pulling the chair to the middle of the room taking the towel “Is there something I need to do? Or not do?” She asked 

 

“Not really, just make sure you wipe down” He said 

 

“Ok” She answered and started drying his feathers

 

“That feels nice, I have Cas do it he’s not as gentle as you” Jimmy said sighing after a few minutes Olive was done she touched where the wing joint attaches to his back “No not there” Jimmy said quickly. 

 

“I’m sorry I didn’t mean to!” She said looking at her hand it was tingling and warm like when he healed her but nicer like being near a warm fire on a cold night “What is this?” She asked 

 

“Well, we have just started the bonding process and if it takes, we will have a glow around us” Jimmy said laughing lightly. 

  
  


“I’m sorry there was some water I didn’t think you told me not to, I’m so sorry!” She said and started to cry, she really didn't mean to what if he didn't want to bond with her what if he decided she was just some sort of freak and didn't want her, or he was angry 

 

“Hey I’m not mad!” Jimmy said softly “It’s just soon that’s all!” He lifting her chin so she would look at him her tail snaked up and wrapped around his wrist holding him tight. “We can finish the bond or we can wait and let it fade” Jimmy said trying to get her to calm down  

 

“What do you want?” Olive asked softly 

 

“I don’t know, I really like you I do, but I don't know yet” Jimmy said “I really like you but a bond is a lifetime commitment and what if you stop liking me!?” 

 

“I don’t see that happening!” Olive said 

 

“Let's sleep on it, we can wait until Cas and Dean to come back and we can all talk about it” Jimmy said and Olive nodded. 

 

“Do you want me to clean under your horns?” Jimmy asked

 

“Yes, please be gentle” Olive said handing him her towel. 

 

“I knew it!” Gabriel said walking in the room suddenly. 

 

“Don’t you knock? What if she was changing!” Jimmy said angrily. 

 

“You bonded with her? You’re both all glowy” Gabriel said amused 

 

“Why are you here?” Jimmy asked annoyed that his brother, even if he was a teacher just barged into their room.

 

“Cas called asked me to check on you two you weren’t answering your phone” Gabriel said 

 

Jimmy had 3 missed calls and bunch of texts, Olive checked her phone it was the same from Dean.

 

“Why didn’t he just summon me if he was worried?” Olive said out loud, 

 

“Maybe he was concerned about how you would arrive if he did… knowing you were with Jimmy?” Gabriel asked “How did it happen?”

 

“It was an accident truthfully, I asked for her help dry my wings and as she was wiping the water away, she touched the bonding spot” Jimmy said 

 

“Just no sex at school ok” Gabriel said smirking 

 

“I wasn’t planning on it” Jimmy snapped back

 

“What!?” Olive asked worried 

 

“To completely bond you two need to have sex” Gabriel said Olive blushed and hid her face Jimmy pulled her to him. 

 

“It’s ok, we won't do anything you don’t want to” Jimmy said kissing her forehead.

 

“Is everyone gonna know?” Olive asked 

 

“Yeah, you have a glowing aura for a while but it will calm down after a few years” Gabriel said 

 

“Great” Olive said just more fuel to added to the ever growing rumour mill.

 

“It’s ok. I don’t care what anyone thinks” Jimmy said

 

“Well, I leave you two love birds alone” Gabriel said with a wink. 

 

Olive had received a very worried text from Dean,

 

**Dean: Olive you better text me Cas is freaking out**

 

**Olive: sorry I was in the shower**

 

**Dean: did you bond to Jimmy?**

 

**Olive: not officially, but I kinda started it**

 

**Dean: what happened?**

 

**Olive: I was helping him dry his wings I don’t really know I touched a part I shouldn’t**

**have I feel horrible what if he doesn’t want to bond with me?**

 

**Dean: it will be ok and from the way Cas is going on I think you two will be fine**

  
  


**Jimmy: hey Cas sorry Gabriel came by the room**

 

**Cas: are you going to officially bond with her**

 

**Jimmy: I don’t know! She feels horrible! And how did you know?**

 

**Cas: just tell her how you really feel about her, and I don't know I just did It was like a rush of power and warmth it was weird**

 

**Jimmy: what if she doesn’t want me**

 

**Cas: she wants you trust me**

 

**Jimmy: fine I’ll talk to her but you need to make a move with Dean!**

 

**Cas: I’m working on it**

 

Olive felt horrible for touching Jimmy where she shouldn't of. 

 

“Jimmy, I am really sorry” Olive said as they got ready for bed 

 

“Olive, it’s ok” He said with a smile.“And it wouldn’t have worked if we didn’t like each other just a little bit” 

 

“Really?” She asked 

 

“Really” He said with a smile, 

 

“Can we cuddle?” Olive asked it always made her feel better 

 

“Of course we can” He said laying in her bed she slid down next to him her tail wrapped around his waist he laughed

 

“What?” Olive asked 

 

“Nothing, your tail…” 

 

“I can move it if it’s weird” Olive said

 

“No way, I like your tail, besides we both know she would just find her way back” Jimmy said. 

 


	5. Chapter 5

**Summary for the Chapter:**

> Olive loses her cool  
> John pays a visit

The school was buzzing with the news that an angel and a demon had started to bond, some were ok with it, others found it strange, offensive even that they would even think of ‘betraying’ their own kind, and others didn't really care.

 

“They don’t have anything else to talk about, do they?” Olive said as they walked to breakfast the next morning, getting into the line to get their food, all around them, students were whispering, 

 

“Her dad is the head of a demon faction” 

 

“What is he going to think?” They were ‘whispering’ like she couldn’t hear them talking about her.

 

“Just breath, they don’t know anything” Jimmy whispered to Olive. She relaxed a bit as he took her hand and gave it a squeeze. 

 

They sat down at a table as far from everyone as they could but Charlie came sat with them smiling happy for the both of them finally together now.

 

“The whole school is talking about you two” She said taking a bite of her food.

 

“Great” Olive said, shaking her head.

 

“Most think it’s nice, I think you are adorable together and you’ll have the cutest babies” Charlie said with a smile Jimmy laughed. 

 

“Let’s not get ahead of ourselves here” He said. It's not that he didn't want to have kids and he had seen angel/demon babies before, rare as they were, they were adorable but Olive and him hadn’t even talked about finishing the bond let alone if they wanted kids. It was far to early for that. 

 

“I can’t believe you would do this!” Lisa said sitting down next to Charlie who rolled her eyes. 

 

“I don’t know why you care” Olive snapped tired of listening to Lisa spew hate.

 

“Because I’m your friend” She said like that answered everything. 

 

“No you are not, you just want to get into Dean pants” Olive said bluntly. 

 

“That’s not true, well it’s true but I am your friend” She said 

 

“No Lisa, you’re not, all you’ve done is boss me around since we met” Olive said getting up to leave.

 

Someone threw something, it hit her in the back of her head. Olives eyes flashed black instantly. 

 

“Who threw that?” She shouted anger rising through her body like flames of a fire “Nobody wants to answer?” 

 

The whole room was quiet as the power rolled off of Olive in waves, everyone could feel it. No one spoke, most avoided eye-contact with her too. But this just made her even madder. 

 

“Olive, it’s ok, I’m here” Jimmy said trying to get her to calm down “Olive look at me” He said. She looked at him but her eyes were still black when she looked down “Sweetheart you have to calm down” He said in a soft voice, hoping that would help.

 

“I’ll make them tell me” She said closing her eyes and focusing on getting the person responsible to confess.

 

A tall blonde haired demon a few tables away stood up suddenly, and struggled to walk forward, it was almost like they were fighting themselves, like their body was out of their control, moved forward by some invisible force. They came to a halt in front of the table and tried to keep their mouths shut, but again, it was out of there control. They couldn’t fight the urge to speak. 

 

“It…. I…” He was struggling not to talk, was fighting so hard his face was turning bright red, you could see the pain on his face as he fought whatever hold she had on him. 

 

“She shouldn’t be able to do that” Charlie whispered looking scared and confused at the amount of power Olive held. 

 

“I…. it was me” The demon finally said breathing a sigh of relief but Olive didn't let go. 

 

“O enough!” Dean yelled popping into the room. 

 

“Dean?” She said and passed out Jimmy caught her.

 

“Damn it” Dean said mad at himself  “Come on!” 

 

Jimmy scooped Olive up in his arms, everyone else in the hall backed up and away from him as he passed by,scared of seeing just a touch of Olive’s powers.

 

“Winchester!” The headmaster yelled 

 

“She can’t control it sometimes, I didn’t think anything would happen while I was gone” Dean said 

 

“I’m going to  have to call your father” Headmaster said shaking his head. 

 

“Go ahead” Dean snapped not really caring at that moment if they called their Dad if not, he followed Jimmy.

 

“Dean, I’m so sorry, I was trying to calm her down” Jimmy said laying Olive in the bed fussing over her making sure she was comfortable. 

 

“Did she take the herbs?” Dean asked 

 

“No, she said she felt fine she said she didn’t need them” 

“This is my fault I shouldn’t have left her” Dean said “What, exactly happened?” 

 

“They aren't happy we bonded, someone threw something. I'm not really sure if it was directed at her but it did hit her and she was already annoyed with Lisa being Lisa and I think it just sent her over the edge” Jimmy said Dean's phone rang. 

 

_ “What happened? John asked  _

 

_ “Jimmy said someone threw something at her” Dean said  _

 

_ “Son, She did take the herbs? Right? _

 

_ “No she didn’t! I think we need to tell her dad” _

 

_ “She’s gonna be angry, I’ll be there in the morning we will tell her together make sure the angels there he can help keep her calm!” _

 

_ “Yes, sir”  _

 

“Dean, what are the herbs for?” Jimmy asked frowning. 

 

“She’s powerful, extremely powerful, the herbs help suppress that side so she can control it better but she's locked in a constant struggle of not wanting to use her powers and totally giving in, I should of told you but everything moved so fast with you two and I didn’t get a chance to let you know everything that goes with taking care of her!” Dean said 

 

“Tell me now,  I’m not leaving her” Jimmy said Dean took a deep breath  

 

“I told you she’s special like really special she has telekinesis, project images into your mind, she can summon anyone or anything at anytime, things bend to her will that’s what happened with that demon, a few other things, She willed him to tell the truth and the more you fight the worse it gets the more painful it gets, my mom did it to me once because I asked her to, so I could understand what Olive could do... I don't envy that demons headache” Dean said rubbing his face.

 

“Ok and I’m guessing it takes a lot out of her?” Jimmy asked, it was a lot to take in demons were not supposed to have that much power anymore.

 

“Yeah sometimes” Dean said looking at his sister, “I'm more surprised that everyone didn't start confessing things, she wanted to truth” 

 

Jimmy's phone buzzed texted from Cas he was worried 

  
  


**Cas: Jimmy is everything alright**

 

**Jimmy: yeah Cas sorry! Olive just had a moment she’s ok now**

 

**Cas: ok have Dean call me**

 

**Jimmy: I will**

 

“Hey Dean give Cas a call he’s worried” Jimmy said

 

“Oh shit!” Dean said pulling out his phone, maybe he liked the angel more than he thought.

 

_ “Hey Cas sorry about that!” _

 

_ “Hello Dean! Is everything alright?” _

 

_ “Yeah Cas everything is fine now” _

 

_ “Ok I’ll see you tomorrow” _

 

_ “See ya tomorrow” _

 

“Dean did she summon you?’ Jimmy asked wondering, Dean had popped up from nowhere 

 

“Not exactly, I was with Cas walking around the museum and than I was in the dining hall I don't know how or why it happened” Dean said not really knowing how to explain his sudden appearance in the dining hall

  
  


Olive slept until the morning Jimmy curled up by her on the floor, by her bed 

 

“Jimmy?” Olive asked sleepy, rubbing her eyes

 

“Hey are you ok?” Jimmy asked

 

“Yeah I think so,  What happened?” She asked 

 

“You…. you willed the room” Jimmy said 

 

“I….. What?” Olive asked in disbelief there was no way she should be able to do that, at least not yet.

 

“Dean can explain it better” Jimmy said as Dean walked in 

 

“Good you are awake dad’s here in the headmasters office” He said 

 

“How bad did I mess up?” She asked scared she may have hurt someone more then they deserve

 

“It’s ok sis you just gotta remember to take your herbs that’s all” Dean said 

 

“Come on dad wants to see you” He added 

 

“Jimmy too?” Olive asked 

 

“Jimmy too! He’s your mate” Dean said Olive nodded and smiled getting out of bed not bothering to change her clothes. 

 

“Daddy” Olive said seeing her dad 

 

“My little demon” John said hugging her tight 

 

“This is Jimmy” She said 

 

“Hello sir” Jimmy said holding out his hand 

 

“Nice to meet you” John said eyeing olives tail protectively wrapped around Jimmy’s wrist 

 

“Behave” Olive said to her tail as it  snaked tighter around Jimmy's wrist 

 

“Fine do what you want” Olive said giving up on trying to get it to behave 

 

“Hello headmaster” Olive said 

 

“Hi” He said with a soft smile 

 

“Olive what do you remember?” He asked 

 

“Well Lisa was being bossy and rude, someone hit me with something and I woke up in the room, how bad?” Olive asked 

 

“You willed the entire room to tell the truth, specifically who hit you” Dean said 

 

“How the hell could I do that mom said that I couldn’t until I was older” Olive said

 

“The herbs it  helps keep everything in check, it’s too much power, demons haven’t had that much power in centuries” John said 

 

“Dad I know! I’m sorry felt fine yesterday it may have just been the excitement because of Jimmy and I, I’m so sorry I won’t skip anymore I promise I don’t wanna hurt anyone” She said panicking 

 

“Olive look at me” Jimmy said she looked up at him 

 

“I’ll help you ok?” Jimmy said smiling she nodded and leaned into him needing to be close

 

“I got you” He whispered. 

 

“What do you mean you know?” Dean asked wondering why his sister never told him that she knew what the herbs were for 

 

“Mom told me before she died,” Olive said tears forming 

 

“It was one of the last conversations we had, she told me all about it and my powers and how they would grow” Olive said wiping her eyes

 

“Why didn’t you say anything?” John asked 

 

“You guys never made a big deal about it so I didn't either” She said

 

“Alright you didn’t hurt anyone and everyone is a little scared of you now but as long as you take your herbs and try to keep everything in check you can stay, I understand you to have started the mating bond?” He stated 

 

“Yeah it was an accident” Jimmy said “but I don’t mind!” 

 

Olive blushed and turned her head 

 

“Daddy are you mad?” She asked not that she was really worried he would hate Jimmy but still wanted to know 

 

“No sweetheart I’m actually really happy for you, Dean showed me a video of Jimmy sticking up for you, I have to say it was quite impressive” John said 

 

“What video?” Olive asked 

 

“Cole got in my face about us and I was angry” Jimmy said.

 

Dean pulled it up and showed Olive, 

 

“Jimmy I don’t know what to say, thank you” She said smiling at him

 

“It’s what I see” He said. 

  
  


John stayed for lunch, as they headed to the dining hall to get their food they heard demons and angels whispering 

 

“Can’t believe he’s fine with it” A demon whispered 

 

“It’s disgusting angel and demon it’s blasphemy” An angel said 

 

“This what it’s always like?” John asked

 

“Pretty much, If they are whispering about dean and I, it’s my horns but now they have new fuel” Olive said 

 

“Hey look Cas is back” She said pointing Dean smiled and took off towards the angel that Dean most definitely did not have a crush on

 

“Cas” He called getting the angels attention he smiled wide at Dean and waved 

 

“Him too!?” John asked

 

“I don’t know” Olive said with a smile Jimmy laughed 

 

“I know Cas likes him but I’m pretty sure it’s one sided” He said Olive shrugged, 

 

John laughed and headed to the table where Dean was sitting, 

 

“Do you have something to share?” Olive teased 

 

“Shut up” Dean said blushing, Cas sat down next to Dean  with his food 

 

“This is our dad John, Dad this Castiel!” Olive said 

 

“Nice to meet you sir” Cas said holding out his hand John shook it

 

“Uh hi I’m Charlie!” she said more excited than normal 

 

“Have a seat” John said 

 

“It’s so nice to meet you! I love what you have done with the whole angels and demons are similar movement ” Charlie said 

 

“Thank you, always nice to see a young demon taking an interest in politics” John said  

 

“Hey sorry about yesterday if I scared you” Olive said 

 

“No worries! I mean it was a little freaky” Charlie said

 

“We are still friends?” Olive asked 

 

“Of course Olive, you’re just super powerful, I wanted to be your friend before why would that change?” Charlie said 

 

“Thanks!” Olive said Charlie smiled. 

 

“Sir Can I speak with you!?” Lisa said walking up like she owned the place 

 

“Go away” Olive said 

 

“I wasn’t talking to you, I was talking to your father” Lisa snapped 

 

“What is it you wanted to speak to me about?” John asked looking at Olives reaction to Lisa 

 

“This is a disgrace to all of demonkind” Lisa said with a huff

 

“I’m assuming you’re talking about Olive and Jimmy?” John said looking at the two of them Olive rolled her eyes and Jimmy wrapped a protective arm around her 

 

“Yes I am” Lisa said 

 

“What about it?” John asked 

 

“You shouldn't allow the pollution of demon blood, what about the children?” Lisa said

 

“And exactly who are you to tell me what should and should not allow?” John asked standing up show his power has head of the demon faction in this territory, he spread his wings in a dominance display he wasn't gonna let some little demon talk to him that way, or talk about his only daughter 

 

“I just… I um” Lisa said looking at Dean who put his hands up as if to say you brought this on yourself should have just stayed out of it

 

“Hey I’m fine with whole thing in fact I hope they finish the bond because first and foremost I’m a father and my daughters happiness comes before anything else” John said 

 

“But he’s an angel” Lisa protested like it was going to make a difference

 

“Yes he is and apparently he knows how to treat a demon better than any of you” John said

 

“So to any of you who has a problem with this bond get over it, they are happy and in truth that’s all that matters, you are dismissed child” John sitting back down, 

 

Lisa scoffed and walked away 

 

“Thanks dad” Olive said

 

“Anything for you,  Now I’m off I gotta get home” John said 

 

“Do you need me?” Olive said

 

“No I have my truck” John said 

 

“Bye daddy” Olive said hugging John 

 

“Dean, Jimmy come on I need to talk to the both of you!” John said. 

 

“Dad?” Dean asked when they finally got to Johns truck 

 

“Here’s the deal what I said there was the truth I really do hope you and Olive bond but there’s a lot we need to tell you, That show was just a touch of her full power, The herbs help but keeping her calm is the best she controls it the best she can but with her mother gone I’m worried, she still grieving and grief does things to us all ” John said

 

“How do I help?” Jimmy asked 

 

“she's head over heels for you, love on her she’s a sweetheart if you want to finish the bond you have my blessing I think it will help her” John said  “just make sure she feels loved and know she can turn to you if she needs to” 

 

“I’ll make sure, I do love her and it’s not just the bond that started it she's special to me” Jimmy said 

 

“Dean” John said

 

“I’ll make sure she doesn’t skip anymore and if I need a field trip again overnight I’ll check in with her and Jimmy” Dean said 

 

“Alright I’ll check in more too, it was a struggle for your mom too I do not envy what they go through” John said feeling guilty for not doing it as often as he like to he need to take time even if he just sent them a text message

 

“Hey breaks coming up for Samhain I want you and Castiel to come to the house” John said

 

“Yeah sure we don’t do anything anyways demon holiday and all I loved to learn about it” Jimmy said John nodded got in his truck and drove off. 

 

“Hey Cas do you really like Dean?” Olive asked 

 

“um yeah!” He said not looking at her 

 

“tell him I’m 90% sure he likes you too!” She said he looked up “we talk he needs a push, his really not that big of a jerk”

 

“really?” Cas asked not knowing what to do with this new information Olive nodded

 

“I would know!” She said smiling wide at him she just wanted them both happy and she knew Dean was happy around Cas weather he wanted to admit it or not 

 

“yeah dean told me you share emotions!” Cas said 

 

“is that all he told you!?” Olive asked wondering what else the talked about

 

“he told me why your dad sent you here” He said Olive nodded

 

“I don’t blame him, sometimes we can’t control it, just keep at Dean he will see you for more than just angel” She said 

 

“I understand” Cas said, Olive sat down on the bed and rubbed her temples 

 

“you ok?” Cas asked 

 

“yeah the herbs make me tired, I think it’s my body compensating for my powers being bound!” Olive said laying down. 

 

Olive fell asleep before Dean and Jimmy came back

“she fell asleep” Cas said Dean nodded 

 

“Jimmy you ok?” Dean asked Jimmy looked worried about all the new information he was getting about Olive 

 

“yeah I’m glad your dad is happy about Olive and I” Jimmy said 

 

“hey so dad wants you and jimmy to come home for the break” Dean said to Cas

 

“I don’t see why not it’s a demon holiday anyways why not?” Cas said 

 

“dad’s not gonna care he’s too busy writing his books” Cas added Jimmy nodded. 

 

“Hey!” Olive said sleepy waking up to the sound of everyone talking

 

“hey yourself” Jimmy said 

 

“you ok?” Dean asked always worried about his sister 

 

“yeah you know the herbs make me tired, what did dad want?” Olive asked sitting up 

 

“he invited Cas and I on break” Jimmy said 

 

“oh” Olive said more surprised then she meant to 

 

“do you not want us to come?” Jimmy asked worried that she didn't want them to come on break with her after all if was a family holiday for demons 

 

“oh no! I’m surprised he invited you that’s all I want you to come I was going to ask him about it!” Olive said, 

 

“so this holiday what is it exactly?” Cas asked 

 

“um we should start learning about it in demon studies but when the humans were here centuries ago they called it Halloween we call it by it's true name Samhain” Olive said 

 

“it’s her favorite holiday” Dean said 

 

“what’s not to like we celebrate like the humans used to spooky stories, candy lots of candy we dress up in costumes like the humans used to do it to confuse the evil spirits but you know it’s still fun Dean and I always win the costume contest every year but I guess we need to get you guys some too! This is going to be so much fun!” Olive said very excited 

 

“calm down” Dean said Olive stuck her tongue out at him. 


	6. Chapter 6

 

The break finally came Olive was very excited to be taking Jimmy and Cas home for a holiday, John had sent a car to pick them up Olive could only transport one at a time the trip always wore her out if she did it too much and she wanted to enjoy her time with Jimmy outside of school and everyone watching them.

 

“Now mom used to decorate the house I don’t know if dad will do it this year with mom being gone” Olive said sounding sad and disappointed

 

“Olive can I ask about you your mom?” Jimmy said she never really talked much about her mom

 

“Um sure she um….. she got sick and than really sick and died!” Olive said looking out the window not wanting to cry this was supposed to be a fun trip not a sad one 

 

“How… how long ago?” Jimmy asked not sure if it was appropriate or not 

 

“About 6 months ago” Olive said

 

“Olive I’m so sorry” Jimmy said no wonder she never talked about her mom the wound was still fresh 

 

“It’s ok, some days are harder than others but we coup” Olive said giving him a soft smile and small peek on the lips Jimmy nodded. 

 

“I take it you and you mom were close?” Cas asked noticing a slight change in Dean, they were in the seats behind Olive and Jimmy 

 

“Yeah we were, all of us, when dad had to work late we um we’d have movie night all kinds of junk food, pie all kinds of stuff, O’s she’s introverted so staying home was more her thing but I’d drag her out get in trouble!” Dean said with a laugh 

 

“Look at those love birds” Dean said pointing to Jimmy and Olive in front of them, changing subject it was hard for Dean to talk about his mom

 

“Shut up, Dean!” Olive said laughing. 

 

They finally pulled up to the house it was to big to be called a house more like a mansion 

 

“Holy mother! You live here?” Cas asked looking out the window in surprise

 

“Yeah look Dad decorated” Olive said pointing to the skeletons, and fake Cobwebs,giant realistic looking black widow on the roof pumpkins lining the walkway and the porch  

 

“It’s huge” Jimmy said trying to get a better look 

 

“Where do you live?” Olive asked wondering why they both were acting like they had never seen a mansion before 

 

“In a regular sized two story 3 bedroom one bath house” Cas said 

 

“Welcome to house Winchester” Dean said smiling. 

 

“Welcome home kids” 

 

“Hi Ellen!” Olive said she was a short brown haired, brown eyed demon with on slightly crooked wing that never set right, and short tail that she had not problem whipping the kids with 

 

“You bonded?” She asked noticing a glow and more power radiating from Olive  

 

“This is Jimmy” Olive said introducing him, 

 

“Welcome” Ellen said smiling 

 

“This Cas” Dean said 

 

“Hi hun!” Ellen said smiling 

 

“I’m made up your rooms?” Ellen said 

 

“Dad here?” Olive asked 

 

“He’ll be home later” Ellen said they nodded 

 

“Go on up, lunch will be ready soon” Ellen said

 

They headed up stairs Olive pulled Dean off to the side to talk to him, telling Jimmy and Cas to go ahead and look around, 

 

“Are you gonna make your move?” She asked 

 

“I do like him” Dean said 

 

“We only need one but two is better” Olive said 

 

“I’ve been a dick to him” said Dean

 

“He will forgive you, just tell him how you feel, he likes you” Olive said 

 

Dean nodded knowing he did actually like Cas and they only needed on angel for their plan to work but two was just icing on the cake. Olive joined back with Jimmy 

 

“This place is huge” Jimmy said looking around Olive smiled 

 

“Game rooms over there” Dean said pointing to a closed door 

 

“My rooms over here and Olive is down the hall” He added

 

“Come on!” Olive said pulling Jimmy down the hall Dean laugh

 

“Excited?” Dean said raising an eyebrow Olive made a face. 

 

“Where am I staying?” Cas asked 

 

“With me, I hope you are ok with that” Dean said walking into his room 

 

“Oh I just thought that you um might want to be alone!” Cas said

 

“Nah man I like having company, I end up in Olives room anyways” Dean said

 

“Wow!” Cas said looking around the room, 

 

it was huge giant king size bed in the middle of the room, black and red comforter with matching pillow cases, posters of cars and bands covered most of the wall on one side of the room bookshelves full of books nick snacks, pictures of him and Olive and their friends, floor to ceiling windows with a door that lead out to a balcony. Large bathroom with a bath and shower enough room in both for a few people.

 

“There extra blankets and pillows in the closet” Dean said pointing 

 

“Ok” Cas said 

 

“I uh have something to tell you” Dean said Cas looked at him 

 

“It’s not bad! I just uh I’m well O has been pushing me and I just um…. it ok if you don’t…. just her and Jimmy and ... uh, um I uh like you” Dean said mumbling the last part

 

“I’m sorry I didn’t catch that last part” Cas said standing closer to him 

 

“I said uh, I… um I like you! Ya know more than a friend” Dean said

 

“It’s totally fine if you don’t…” Cas cut him off 

 

“I like you too Dean!” Cas said stepping closer

 

“awesome” Dean said smiling. 

  
  


Olives room was a little bit smaller than Dean's but still impressive, king size sleigh bed pushed against the wall, purple and black covers, matching pillow cases, a teddy bear with horns and a tail sat on the bed, Bay window show a balachany that wrapped around the house.

 

“Olive, I am sorry about your mom” Jimmy said feeling bad for his mate 

 

“If it's ok, I don’t really wanna talk about it right now but I promise I will tell you all about her, she would have like you!” Olive said with a smile 

 

“my love it is totally fine!” Jimmy said wrapping her in a protective hugging her, 

 

“so this giant house for the four of you?” Jimmy asked 

 

“And the staff they are family too! Ellen and Jo moved in when jo’s dad passed, um let’s see there’s Frank he does Surveillance he’s a bit paranoid but we love him, Uncle Bobby he works on the cars but him and Dad have been friends forever, Ketch head of security he’s a pain but it’s fun ditching him!” Olive said laughing

 

“That’s mean!” Jimmy said laughing they didn't have security either their dad was too cheap or they were not important enough for anyone to kidnap

 

“You haven’t met ketch” Olive said

 

“Ok who else lives here?” Jimmy asked 

 

“The Gardner but he lives outback keeps to himself mostly, and that’s it! Oh and there’s a few live in maids but we don’t really see them too much which I guess is part of the job!” Olive said shrugging lay on the bed yawning 

 

“Tired?” Jimmy asked 

 

“I hate the herbs, it make me tired it’s why I nap all the time and miss out on everything ” She said

 

“It’s ok! You nap I’ll go find our brothers” Jimmy said 

 

“Our rooms are connected” Olive said pointing to a small door 

 

Jimmy laughed he wasn’t surprised they were best friends and Dean spoiled her 

 

“What?” Olive asked looking confused why he was amused by this information

 

“Nothing I’m...” He said as the door opened 

 

“See Olives room” Dean said 

 

“Hey!” Dean said “I didn’t think you guys were here”

 

“No worries I was gonna take a nap, I was just telling Jimmy about the door!” She said

 

“Come on, I'll show you around while O naps!” Dean said Jimmy nodded

 

“Have a good sleep!” Dean said Jimmy kissed her gently 

 

“Wake me up for food!” She said leaning back against the pillows . 

  
  


Jimmy followed Dean and Cas out of the room, they headed down the hall towards the stairs showing them the different rooms

 

“I feel bad she’s always napping!” Dean said

 

“She said it's the herbs make her tired” Jimmy said 

 

“I know this is a lot but really we are just normal, umm we have bathrooms in our rooms, let’s see game room/ entertainment room we will go in when O wakes up she’s always in there reading or watching a movie, kitchens this way!” Dean said heading toward  the stairs to take them to the kitchen

 

“You boys hungry?” Ellen asked spotting them walking the kitchen 

 

“Should I wake up Olive?” Jimmy asked 

 

“No let her sleep it's not ready yet” Ellen said 

 

“Poor thing! Doc up the dosage agian” Ellen asked with annoyance in her voice 

 

“Yeah she’s more powerful than mom was, she more tired she just needs to adjust!” Dean said 

 

“You didn’t tell her?” Jimmy asked 

 

“I did, She didn’t tell you?” Dean asked 

 

“No” Jimmy said a bit disappointed 

 

“She probably just didn’t want to worry you, don’t be mad at her!” Dean said

 

“I just want her to tell me herself” Jimmy said annoyed that she would keep this from him they were supposed to be mates, they could tell each other everything

 

“She has a hard time, she feels like everyone treats her different except you and if she didn’t tell you because she doesn’t want to worry you!” Dean said Jimmy nodded 

 

“I’m sorry, I’m not mad just worried!” He said, understanding that something are hard for Olive

  
  


“Go get your sister! Food ready!” Ellen said Dean nodded and headed up to get Olive 

 

“So you boys excited about learning a new holiday?” Ellen asked

 

“Yeah actually we are!” Cas said 

 

“I’m sorry I’m having a hard time tell you apart!” Ellen said 

 

“I’m Cas!” Ellen nodded 

 

“so that means you and Olive!” Ellen said looking at Jimmy

 

“It’s not complete we um need to uh….” Jimmy said Ellen nodded 

 

“Probably not appropriate at school!” She said with a wink Jimmy blushed, 

 

“What are you doing to my boyfriend?” Olive asked walking into the kitchen 

 

“Nothing, go sit I’ll bring it out!” Ellen said smiling at her 

 

“We can help!” Jimmy said they always had chores at home 

 

“Nope go!” Ellen said 

 

“It’s best to just do as you are told!” Olive said her tail snaked around his wrist Ellen raised an eyebrow it wasn't like Olive to be so affectionate in front of everyone

 

John came home for lunch, and to see his kids happy they were home 

 

“Hey dad!” Dean said 

 

“Glad you made it ok, Olive can I speak with you?” John asked when they were done with lunch

 

“Yeah dad is everything ok?” She asked 

 

“Come on” He said smiling they walked down the hall to johns office 

 

“Oh so it’s official business we need to discuss?” Olive said teasing her dad 

 

“Your such a pain sometimes” He said opening the door

 

“Yes, but you love me all the same” she said 

 

“I know Samhain is going to be hard for you this year” John said Olive nodded 

 

“Thank you for decorating, I wasn’t sure if you were going to” She said 

 

“Um you and Jimmy while your here if you want to complete the bond I have no objections!” John said 

 

“Ew dad, I don’t want to talk about this with you!” She said blushing her tail wrapped around her neck and rubbed her face

 

“How are things with you and Jimmy?” John asked 

 

“Good actually,  about the same at school, they still aren’t happy about it” Olive said annoyed

 

“As long as you're happy and Jimmy’s happy that’s all that really matters!” John said 

 

“I haven’t told Jimmy about the increase, do you think he’ll look at me different?” Olive asked 

 

“No, he loves you, tell him before some else does!” John said Olive nodded

 

“Go on i just wanted to check in” he moved his hand motioning her to get out of his office 

 

Olive walked back to the dining room, happy her dad didn't keep her any longer

 

“Hey we were just headed to the game room!” Dean said 

 

“Meet you there, Jimmy can I talk to you?” Olive asked nervous about telling him about the increase 

 

Cas and Dean headed to the game room, but they both really wanted to know what they were going to talk about 

 

“What’s up?” He asked taking her hands 

 

“Um I should have told you this sooner but I was embarrassed the doc,he increased my herbs!” Olive said 

 

“It's ok!” He said smiling 

 

“Thank you for telling me” He added looking a bit sheepish  

 

“Who told you?”

 

“Don’t be mad it was an accident they thought I already knew!” Jimmy said 

 

“I should've just told you, are you mad?” Olive asked

 

“No baby I’m not mad, I just want you to know you can tell me this stuff I can't help you if I don't know about it” He said hugging her, 

 

“It's just hard” she said playing with her tail, she did really care about him 

 

“Come on!” He said picking her up and through her over his shoulder she squealed with laughter 

 

“Dean, this is amazing!” Cas said looking around the game room, a huge TV hung on the wall a cubby of game systems and a blueray player under it, one wall was lined with bookshelves lined with books, little things here and there

 

“O and I are a bit spoiled!” Dean said smiling 

 

“All these books, are they…” 

 

“Really old? Some of them” Olive said walking into the room 

 

“Jeez” Jimmy said looking around surprised they had the living room with an old TV and an even older game system that only worked when you blew in the cartridge 

 

“We are spoiled we know!” Olive said smiling at him 

 

“How many game systems do you have?” Jimmy asked looking at all of them 

 

“Oh great, you're gonna steal my boyfriend with your collection of gaming systems” Olive said teasing Dean 

 

“I’m not going anywhere you’re stuck with me!” Jimmy said grabbing her and pulling her close 

 

“oh really!?” She asked kissing him, 

 

“Get a room!” Dean said with a smirk 

 

“Are we gonna watch a movie or what?” Olive asked

 

“Fine! What are we watching?” Dean asked 

 

“Don’t care just put something on” Olive said pulling Jimmy to the couch, 

 

“I guess I should have told you about all this!” Olive said feeling bad that they were so spoiled and Jimmy and Cas didn't have as much 

 

“Isn’t your dad the like head angel or whatever?” Dean asked usually the heads of the factions were loaded 

 

“Yeah but he also likes to be a broke writer!” Cas said annoyed that his father could care less about anything other than his books and stories

 

“I don’t know what that means?” Dean said sitting down next to Cas turning the movie on 

 

“Dad would rather hide in his study and come out when he needs to for angel stuff!” Cas said 

 

“It’s why we live in a small three bedroom house and one of those rooms is his office” Jimmy said 

 

“We are supposed to live humble lives nothing flashy” Cas said using air quotes 

 

“But how will the other respect you!” Olive asked 

 

“They don’t, Raphael our oldest brother basically runs everything” Cas said 

 

“He sent us to the school said it would look good!” Jimmy said 

 

“Hey I am sorry we didn’t think that it would be a big deal!” Olive said 

 

“Baby, it's not a big deal we just live different, I don’t love you less or different because your dad spoils you or you have your own game room I don’t care if we could live in box as long as I’m with you!” Jimmy said Olive smiled at the way he makes her feel like the most special demon in the whole world

 

“Damn jimmy you should be a poet!” Dean said 

 

“Shut up!” Olive said glaring at Dean “I love you too!” Olive said smiling 

 

“Oh my god! Just go get it on already!” Cas said, 

 

“Why don’t you two get it on already?” Jimmy snapped back, Cas looked at him 

 

“Wow! That was rude!” Cas said 

 

“I’m sorry”Jimmy said feeling bad that he snapped. 

 

Ellen came and got them for dinner, she pulled Olive off to the side 

 

“How's it going?” Ellen asked 

 

“Perfectly as planned but Dean almost messed it up, he actually likes Cas, you know Dean expressing himself in the right way is always hard for him but we are back on track and hopefully Jimmy and I will complete the bond” Olive said 

 

“Good girl your mama would be so proud” Ellen said smiling 

 

“Thanks Ellen” Olive said 

 

Olive and Ellen joined everyone in the dining room 

 

“So we are having a Samhain party!” John announced

 

“Really Dad!?” Olive asked excited

 

“Yes! Really I know how hard it is without you mom but I know it’s your favorite holiday too!” John said smiling 

 

“Thanks dad!” Olive said smiling she looked at Dean 

 

“Dean are you ok!?” Olive asked

 

“Yeah it’s just hard that’s all!” He said not looking at her

 

“I’m sorry!” Olive said 

 

“No O it’s ok be excited, this is something you and mom shared and this is to honor her than do it!” Dean said Olive nodded pushing her food around her plate 

 

“O please don’t feel bad for being excited!” Dean said she nodded 

 

“Sweetheart!” Jimmy said rubbing her back “it’s ok!” 

 

“Cas and I honor our mom differently!” Jimmy said 

 

“Jimmy’s right he does his own thing I do mine!” Cas said shrugging 

 

“Dean I thought that you and Olive both…” 

 

“Dad it’s fine really! Olive always enjoyed it no reason for her to stop!” He said getting up and leaving 

 

“Dean?” Olive asked “shit!” she knew how much their mother’s death affected Dean and it was still a fresh wound 

“I can…” she started 

 

“Leave him!” John said 

 

“If it gets too much for you do but tell him before you do!” John said Olive nodded 

 

“Do what?” Jimmy asked confused at the lack of information 

 

“I can take his emotional pain just small amounts!” Olive said 

 

“I didn’t know you could do that!” Jimmy said 

 

“It’s a demon twin thing!” John explained 

 

“there a lot about her you don’t know but you’ll learn, I been with Mary 15 yrs and still finding things out about her!” John said Jimmy laughed 

 

“I guess you're right and we will have our whole lives to learn about each other!” Jimmy said smiling Olive smiled back 

 

“Cas will you go check on him?” Olive asked 

 

“Yes!” Cas said smiling. 

 

Cas found Dean in his room, sitting on his bed crying 

 

“Hey!” Dean said wiping his eyes 

 

“Hello Dean!” He said 

 

“Sorry man I just i feel so guilty Olive doesn't know and I don't wanna tell her” Dean said 

 

“Know what Dean!?” Cas asked sitting down next to Dean on his bed 

 

“How mom really died” Dean said shaking his head 

 

“What does she think happened?” Cas asked

 

“That she got sick, than died from the sickness but that's not what happened, she killed herself, she was in so much pain ”  Dean said Cas looked at him 

 

“Dean I’m sorry, but why didn't you tell Olive I'm sure she could handle it” Cas said placing his hand on Dean's, Dean held his hand 

 

“Dad said not to that she was too fragile, it would send her over the edge and she wouldn't come back from it so if she thinks it was the sickness that killed her it would be better” he said 

 

“I won't say anything to her or Jimmy, I promise but I do think you should tell her it's only fair” Cas said

 

“Thank you, and you are right I'll talk to my dad about it” Dean said leaning in and kissing him Cas was startled at first but relaxed into the kiss, it was the most amazing feeling something Cas had been wanting for a while to know how Dean's lips felt on his, the world slowed, it amazing how soft Dean's lips were, plump they felt again his, Cas could hear the blood rushing in his ears the way his breathing was picking up and then it stopped, he sat there with his eyes closed for a minute

 

“I’m sorry!” Dean said pulling away quickly embarrassed, hoping that Cas wouldn't get offended  

 

“I enjoyed it!” Cas said smiling 

 

“Really?” 

 

“Yeah Dean I told you I like you too” Cas said

 

“I don’t understand Cas, I was a jerk to you the first few weeks of school” Dean said 

 

“I know but I knew under that prickly exterior there is a sweet loving demon who cares deeply for his family, especially his sister!” Cas said smiling 

 

“So uh you wanna be my boyfriend?” Dean asked looking him straight in the eyes with a confidant almost cocky smile 

 

“Yes!” Cas said smiling. 

 

Jimmy, John and Olive were still sitting at the table finishing their food when John finally spoke up

 

“I need to get this off my chest!” John said 

 

“What dad?” Olive asked worried something had happened 

 

“I was angry at first when I found out about you and Jimmy!” John said Olive looked at John 

 

“Don’t get upset just let me finish” John said looking at her

 

Olive looked at him, eyes flashed black before going back to green 

 

“It’s because you are young and my only daughter!” John said “it has nothing to do with species”

 

Olive relaxed still a bit annoyed that her dad would be upset because she wanted to mate with someone 

 

“I’m not angry anymore I see how much he cares for you besides I think he will be good for you” John said Olive nodded 

 

“I’m gonna go check on Cas” Jimmy said getting up kissing the top of Olives head, not wanted to be a part of this very awkward conversation 

 

“If you decide to follow through…” 

 

“Dad!” Olive whined, she wanted him to stop bringing it up 

 

“No sweetheart you need to know this, you’ll need to have sex at least twice a day it’s a horned demon thing, it will help with the herbs but releasing all that built up energy will be good for you and you won't need to nap as often,  you’ll have to soundproof the room” John said 

 

“Dad, I don’t know if  _ he  _ wants to!” Olive said 

 

“Olive that boy is in love with you and I’m sure he was before you touched him!” John said 

 

“I don’t know, I mean I want to with him but I just he’s holding something back and I don’t know what it is?” She said 

 

“Ask him!” John said

 

“I’m gonna head up, do you want help?” She asked pointing to the dishes on the table 

 

“No, go on!” John said. 


	7. Chapter 7

**Notes for the Chapter:**

> I mixed up the chapters sorry if you have read this already go read six and then seven it will make more since

**Chapter 7**

 

“Olive is this really necessary?” Cas asked a little embarrassed at their topic of conversation 

 

“Uh yeah!” She said as if Cas should already understand what she was talking about

 

“There going to be a bunch of Demons all over him you need to let them know he’s not on the market anymore that he is yours and you are his” Olive said 

 

“I don’t know! I mean I’m not a virgin but I just I wanted to take it slow with him” Cas said

 

“Well just make sure you let them know he’s yours!” Olive said Cas looked at her 

 

“Why is it so important to you?” Cas asked

“I know how much you like him, I don’t wanna see you get hurt because some bitch is all over Dean!” She said Cas nodded 

 

“ I can be a bit sensitive” Cas said Olive smiled, she knew Dean and sometimes he was dumb when it came to flirting. 

 

Olive went to find Jimmy, he was in her room reading a book on the bed 

 

“Hey baby” He said putting his book down 

 

“Hello” She said with a smile

 

“So the party tonight?” Jimmy asked walking to her

 

“What about it?” Olive asked 

 

“I want to know what to expect is all!” Jimmy said brushing her hair behind her ear letting his

hand linger just a bit, brushing his fingertips lightly down her neck she sighed loving the feeling of his touch no matter how small it was 

“O, well there’s drink and food and dancing, little demons come to the door for candy” Olive said smiling 

“Do I have to worry about other demons?” Jimmy asked 

“No, you know I love you” Olive said confused at why he would ask that 

“That’s not what I mean” Jimmy said 

“There’s always one ass” Olive said Jimmy nodded 

“Well, I guess we need to finish the bond” Jimmy said with a smile Olive laughed as he backed her up towards the bed 

“You’re serious?” She asked nervous and excited 

“Yeah I am” He said capturing her lips in a heated kiss Olive pulled away 

 

“I’ve never…” she said looking away a bit embarrassed 

“It’s ok, I got you” He said leaning back down the kiss her 

“Wait you’ve..” Olive asked surprised but kind of relieved that he would know what he was doing 

“It's fine, is that what you’ve been hiding?” She asked he nodded 

He walked her backwards towards the bed hands never leaving her face, he pulled away to pull her shirt over her head gently, she shivered when the cool air in the room hit her skin, he pulled his own shirt off eyes never leaving her face looking for any sign she wanted him to stop, there was none he pushed her back a little more so the back of her knees hit the bed.

 Olive looked up at Jimmy with wide green eyes excitement a nervousness roll off of her he placed his hand on her face a rubber her cheek with his thumb they stood there like that for a moment just taking each other in, Jimmy pushed her shoulders back, she allowed herself to fall backwards on the bed legs hanging off the side he smiled down at her his wings extended behind him, he looked beautiful the way the light reflected off the wall behind him gave him an ethereal look totally and completely angelic taking Olives breath away she couldn't be happier in that moment, Jimmy nudged her legs open with his knee so he could lay on top of her, she was a bit shy about it but he laid on top of her anyways,

“Tell me if you want me to stop and I will” he said brushing the hair away from her neck 

“Ok I will” she said 

 feeling a bit overwhelmed at the sensation of him being on top of her, she also loved the feeling it made her feel safe and warm, cared for. Jimmy pressed a kiss to the concern of her mouth she turned to kiss him back but he moved across her jaw, his skin was soft against hers his hand on her hip she could feel him slid his hand up her stomach a cup her breast threw her bra she bite her lip letting a small sigh escape he smile against her neck, 

“That feels nice” she said 

“Let get this off” he said 

pulling her up to undo her bra, she slid if down her arms feeling a bit selfconoius she crossed her arms trying to hide 

“Don't hide from me, baby” he said moving her arms laying her back down he held her arms above her head 

“What's this?” he asked spotting the odd shaped birthmark she had on the left breast 

“It's just a birthmark” she said smiling

“You are beautiful and all mine” he said kissing back down her neck, kissing and sucking as he went, she couldn't help but try to get some friction between her legs, he knew what he was doing driving her crazy he smiled when she moaned as he made his way down her body, kissing in all the right spots he reached the top of her jeans, he looked up at her she nodded before he undid her jeans he kissed her belly button making her giggle, he smiled wide at her as he pulled her jeans off along with her underwear, she closed her legs not really knowing what she should do  as he took his pants off,

“Move to the middle” he said getting her away from the edge of the bed making sure she was comfortable, 

she laughed a bit when he laid down on top of her, he kissed her deep, loving a passionate, his hands slid down her side make her skin feel like it was on fire, her tail snaked up running the tip through the feathers on his wings he groaned kissing her harder,

“Jimmy” she moaned out he kissed her neck, she ran her fingers through his hair pulling lightly growing impatient she flipped him on his back, he laughed and ran a hand up her back feeling her wings making her groan, her wings were soft, leather like. His hands felt amazing but she wanted more, she smiled at him, he was beautiful and perfect for her he rolled her back over looked at her, she rolled her hips up trying to give him a hint to get things moving, Jimmy smiled 

He lined himself up and slid in Olive moaned and arched her back a bit

“You ok?” he asked 

“Yeah keep going” she said 

He slid out slowing and back out kissing her, she could feel the warmth of the bond growing stronger, feel his grace and her powers swirling together the feeling was intoxicating she flipped them climbing on top Jimmy laughed at the action she loved him up and sank down, Jimmy groaned and swore Olive smiled and started moving her hips in circles, Jimmy grabbed her hips to pick up the pace, her wings spread out behind her 

“Fuck, you are beautiful” he said watching her bouce up and down 

“I'm close” she said 

“Keep going me too” 

A few mover movements and she came muscles squeezing Jimmy's cock pushing him over the edge, Olive giggled and laid down on top of him,

“You ok?” Jimmy asked 

“I’m more than ok!” Olive replied with a big smile kissing Jimmy’s chest 

“you’re stuck with me for life now!” Olive said smiling

“more like you’re stuck with me!” Jimmy said smiling at her, her tail snaked up Jimmy’s body 

“what?” He asked it nudged him 

“I don’t know what she wants!” Jimmy said

“she wants a kiss!” Olive said 

“oh she does, does she?” Jimmy smiled and gave her tail a quick peck it settled on his chest, Olive snuggled closer

“now!” She said out loud and then was gone with the blanket. 

“Son of a bitch!” Olive yelled “really!?” 

Dean standing in the dining room looking a bit embarrassed he didn't even think that Olive and Jimmy may have been in the middle of something

“sorry you weren’t answering the door! I didn't realize” Dean said 

“and you didn’t take that as a clue that I might be busy, you didn't notice?” She yelled extremely annoyed that he would summon her because she didn't answer the door

“I didn’t mean to embarrass you” Dean said 

“good thing I grabbed the blanket” She said 

“what do you want?” She asked annoyed

“here are your herbs” Dean said hoping that would sooth her temper

“Dean this couldn’t have waited” Olive said taking them from Dean

“Dean really what did you want?” She asked taking her herbs, 

“um well it was just um well I uh…” dean said blushing “I needed to talk to you just you!”

“Ok my dear brother what couldn’t wait?” Olive asked wrapping the blanket tighter around herself

“um it’s about Cas” Dean said 

“what about him?” 

“I… did you tell him to basically jump my bones” Dean asked 

“yeah why?” She asked shrugging  “is there food I'm starving?”

“don’t change the subject!” Dean said

“what Dean I just gave him a push, so did you?” Olive asked

“uh yeah we did, I just didn't think that it would be that quick I know we need them but I kinda feel bad” Dean said Olive smiled 

“Don't feel bad your not the one that enacted a mating bond. So from here on, we will try not to summon each other and by the way I'm going to cast a  soundproofing spell for my room!” Olive said smiling 

“that good!?” Dean asked she blushed “he was your first, I hope it was good!” Dean said

“I will tell you all about it later and yeah it was good” Olive said laughing. 

  
  


“You finished the bond!” Ellen said walking into the dinning room, noticing the new since of power radiating off of Olive

“congratulations!” Ellen said hugging her 

“thanks Ellen is dad around?” Olive asked

“no he went out for a bit” She said it seemed like she wanted to say more but didn't 

“So where’s your boy?” Ellen asked 

“upstairs” she said 

“go get him food ready and than party tonight” She said. 

After lunch Jimmy and Olive went off their room to get ready while Dean and Cas went to theirs to change into their costumes

“Are costumes really necessary?” Cas asked Dean

“yes and Olive will kick your ass if you don’t show up in one!” Dean said smiling

“I don’t understand why?” Cas said 

“because it’s tradition and O likes it so something we go with!” Dean said

“you spoil her” Cas said

“yeah I know but she’s my sister, and she’s kind of scary when she is mad” Dean said adding the finishing touches to his costume 

“I don’t understand why I have a harp?” Cas said

“it’s a joke humans thought angels playing harps and had halos!” Dean said smiling Cas shook his head making the halo bob up and down he, followed Dean down stairs to help hand out candy

“what are you?” Cas asked 

“I’m a zombie” Dean said like Cas should have known

“I don’t know what that means” Cas said 

“dude seriously? You know all this other stuff but you don’t know what a zombie is?” Dean asked 

“no Dean I do not!” Cas answered 

“it’s an undead thing!” Dean said Cas nodded. 

Olive and Jimmy were already downstairs handing out candy, Olive was dressed a pinup zombie, tight a-line skirt, corset top, black and red high heels matching the rest of her outfit and Jimmy matched Cas in his mock angel costume

“look at how cute you look!” Olive said smiling at Cas

“I still don’t understand” He said

“it’s supposed to be fun” Olive said Cas nodded 

“I’m sorry, You change if you want” Olive said worried she may have upset him 

“I’m fine, I’ll get used to it” Cas said smiling, they handed out candy for a few hours before guest for the party started to arrive, 

“I’ll be upstairs for a minute” Olive said

“baby, you ok?” Jimmy said concerned about Olives sudden change in mood

“I just need a minute” Olive said tears forming 

“oh, I’ll come with you!” He said 

“no, I need to be alone just for a minute I’ll be ok!” She said he nodded 

“if I need you I can summon you to me!” She said 

“ok promise you will?” Jimmy asked feeling a bit rejected he was supposed to help her with this kind of stuff

“I promise” She said heading up the stairs. 

  
  
  


Once in her room she shut the door she walked over to the bookshelf she kept her mom’s pictures

“Mama I can’t do this” Olive said crying to her mom’s picture 

“I need you mama” She said wiping her tears away with her hand trying not to smear her make-up

“O” dean said 

“what? I didn’t…” 

“I felt your sadness, I need to make sure you were ok?” Dean said walking to his sister 

“I’ll be ok, I just needed a minute!” She said hugging him 

“I know it sucks I miss her too” Dean said 

“I know I just needed a minute alone I miss her so much” She said 

“Do you need more?” Dean asked taking away a bit of her emotional pain 

“no but I will let you know if I do!” She added, Dean kisses the top of her head and lead her out the door. 

“There they are” John said spotting them walking down the stairs 

“hi dad!” they said in unison

“you ok?” John asked 

“yeah dad I’m good, I’m gonna find Jimmy!” She said

“they finished the bond!” John said noticing the difference in his daughter

“this morning actually” Dean said smiling, 

“good this should help her keep calm” John said 

“What does she need to be calm for?” Dean asked very confused by this statement

“Hello John this must be Dean!” 

“Naomi!” John said hugging the Angel 

“yes this is Dean and his sister is over there with her mate Jimmy!” John said Cas made his way over to Dean 

“hey!” Cas said

“this is Dean's….” John said 

“he’s my boyfriend! Castiel!” Dean said holding Cas’ hand

“how progressives both children and it would seem Jimmy and Olive have completely bonded!” Naomi said 

“they fell in love” Dean said 

“you didn’t tell me she has horns!” Naomi said

“do not bring them up” Dean said defensively knowing how Olive hated when people drew attention to her horns

“I didn’t mean anything I…” Naomi said 

“she just sensitive about em” John said dismissing Dean's statement about his sister

“O! Come here” Dean yelled Olive looked up and smiled whisper to Jimmy and tugged him along. 

“This is my daughter Olive, Olive this is Naomi!” John said

“nice to meet you!” She said not letting go of Jimmy hand

“hi I’m Jimmy!” 

“Hello, I see you two have bonded that’s a big step for ones so young!” She said kind of like she was judging them 

“yeah well when you know” Jimmy said pulling Olive close to his side

“what a pretty necklace” Olive said with a hint of sarcasm 

“Olive!” John warned

“I could have swore mom had in just like it, Dad doesn't that look like mom’s necklace?” Olive asked

“not the time!” John said Jimmy squeezed Olives hand her tail wrapped around his wrist

“when is the time dad? You invited her, who is she?” Olive said almost loud enough to cause a scene

“Olive my love, let’s get a drink!” Jimmy said kissing her forehead trying to diffuse the situation  

“no I want him to answer my question” She said looking at John eyes turning black she did enjoy this part 

“Don’t fight it dad, I wanna know too” Dean said 

“Olive stop” Jimmy said turning her head towards him her eyes were black 

“Dammit” Jimmy said  “I can't stop her, answer John” He said 

“she’s… I… she's my new Wife” John finally got out 

“”when? Don't fight it dad” Olive said 

“last month” He said Olive shook her head grabbed Dean's hand and disappeared. 

“What did she do to you?” Naomi asked 

“she willed him to tell the truth, Next time just answer I can’t stop her once her eyes go black” Jimmy said annoyed at the both of them for pissing off his mate

“I wanted to wait, this is her favorite holiday, I didn’t want to ruin it!” John said rubbing his temples,

“Well good job that's exactly what you did, now I'm gonna call Dean and see if they are somewhere we can drive to, really tacky show up in their mom’s necklace” Cas said walking away angry

They were at their moms grave, 

“how could he do this?” Olive yelled trying to not let her powers take control, the haze caused by the herbs was making it hard 

“Olive you gotta calm down” Dean said worried about what would happen if she let her anger get the best of her

“bullshit!” She yelled releasing  some of the built up anger blowing back the trees in the cemetery they made a creaking noise like they were about to fall over

“O” Dean said grabbing her pulling her to him hold her tight

“how could he? How could he do this to her?” She asked tears falling 

“I know, this is why we are trying to get him out remember that” Dean said holding her as she cried his phone rang 

“we are at the cemetery!” He said putting his phone away Olive fell asleep crying against her brother, he patted her head and held her close until Jimmy showed up with a car. 

“She ok?” Jimmy asked 

“hurt emotional but ok otherwise” Dean said laying her in the backseat

“I’m sorry it’s like once her eyes turn black I can’t get her to back off!” Jimmy said 

“it’s up to her too if she wants to and truthfully I’m glad she did it!” Dean said looking in the backseat at his sister

“it was really  tacky, showing up in your mom's necklace” Jimmy said  “um so she lives at the house by the way”

“what!?” Dean said shaking his head in disbelief 

“yeah Cas and I got the whole scoop when Olive took off, she lives in the house but your dad wanted to ease you guys into it so Olive wouldn't, well…” 

“be Olive and lose her cool?” Dean asked

“yeah but I don’t blame her this time I would be upset too!” Jimmy said pulling up to the house. 

“Dean?” John said relieved that they were back and safe

“I'll take her up” Jimmy said taking Olive from Dean 

“is she ok?” John asked 

“No dad she’s not ok! She pissed! And I don’t blame her!” Dean said John looked around not wanting to upset their guest

“come on” He said motioning for dean to follow him, they went to his office 

“you had to of known Olive was going to notice” Dean said kind of wondering why his dad  wouldn't take into account that Olive would notice her own mother necklace John sighed

“I thought that the angel would keep her calm” John said 

“how’s your head?” Dean asked knowing the full extent of how bad of a headache you can get from restiting  Olive’s ability to bend you to her will

“it’s fine, I can’t believe how much that hurts!” John said

“the more you resist the more it hurts, you should've just told us!” Dean said,

A light knock came from the door they waited for John to answer 

“come in!” John said 

“good you’re back!” Naomi said sounding relieved but the relief never reached her expression walking in 

“I don’t understand when did you meet?” Dean asked, when the hell did all this happen, their mom died six months ago when did their dad have time to meet someone new?

“when your mom went to the hospital” John said Dean scoffed

“and what!? You just feel in love while mom was sick dying? And you thought oh look I have a replacement for my sick wife?” Dean asked 

“it wasn’t like that, it just happened” John said taking Naomi’s hand 

“you sister, that power it’s too much for one demon,” Naomi said. 

“you leave Olive alone” Dean said getting angry 

“ignore her” Olive said popping in next to him 

“young lady” Naomi said 

“you are not my mother!” Olive snapped, eyes flashing black 

“Olive enough” Jimmy said walking into the office 

“Jimmy I… I’m sorry” She said

“come here” He said holding out his hand, she went to him 

“I understand you’re angry, but punishing them isn’t going to help!” He said 

“it might!” She said with a soft smile kind of hoping he would agree and let her have at it

“come on let’s get you some herbs and go to bed, I rub your back how you like!” Jimmy said 

“promise?” Olive asked

“I promise but only if you come with me right now and we will talk about this in the morning!” Jimmy said Olive squinted at him 

“fine but I get more than a back rub! For not making anyone's head explode” She said Jimmy smiled and pulled her out of the room. 

All the guest left only a few talking about Olives little temper tantrum.

The next morning Dean went to find John to talk about what happened and what he meant by he thought the angel would keep her calm

“Is this why you wanted her to complete the bond!? Because you thought that Jimmy could manipulate her into not using her powers?” Dean asked finding his father in his office

“yes! Dean She has so much power, she needs him!” John said with enrest

“so that’s why your so ok with it!? I’m your pawn, good thing I do actually love her!” Jimmy said shaking his head, after over hearing them talking about him

“Are you going to tell her?” John asked

“no I’m not you are!” Jimmy said leaving Olive was outside the door he ran into her

“hello my love! I thought you were sleeping!” Jimmy said 

“I woke up and you were gone!” She said with a bit of a pout, 

“I’m sorry! Where’s Cas!?” He asked 

“I’m the game room!” She said

“than let’s go!” Jimmy said

“but what about dean?” She asked 

“he’ll be up in a minute!” Jimmy said with a smile she smiled back, she ran her hand down his wings

“don’t tease me” He said with a small growl 

“I would never” She said with fake surprise as they headed back up the stairs Ellen came out of the dining room 

“Olive!” Ellen called

“yes!” She answered 

“foods ready!” She said

“ok!” She said 

“I’m gonna get Cas!” Jimmy said letting go of her hand. 

Olive headed to the dining room to sit down to breakfast

“Olive can I talk to you?” Ellen said, hoping she wasn't overstepping her place but she had been there for their births watched them grow, held Olive when she found Mary dead in her bed

“of course Ellen you know that!” Olive said, she 

“it’s about what happened last night!” She said

“go ahead!” Olive said kind of annoyed even thinking about what happened, how her father betrayed their mothers memory, that angel showing up in her mother’s necklace acting like she was in charge

“I don’t wanna over step and I know how close you and your mama were, but just give her a chance ok? Please? I know it's a big kink in the plan” Ellen asked 

“Ellen you know I respect you but she showed up in mama's necklace, mama hasn’t been gone that long and they are already married! I’m not ready to even think about dad with someone else” She said

“ok sweetheart I understand, but for this to work I need you to control yourself. I know how hard you are fighting the effect and they push more on you but I need this from you” Ellen said 

“O I will try not to use my powers on her” Olive said Ellen laughed as they walked into the dining room 

“you could have given me a heads up!” Olive said 

“play nice” Ellen said Olive pouted. 

“Good morning Olive” Naomi said 

“Naomi” She said taking her seat 

“I want to talk to you before your father gets in here!” Naomi said

“about what?” Olive asked 

“your attitude for one” Naomi said 

“oh I’m sorry! I had no idea that my father married someone, you had the nerve to show up in my mother’s necklace who died 6 months ago but yes let's talk about my attitude” Olive said 

“John should have told you, but I expect you to respect me in this house” Naomi said 

“I don’t know why you think….” Olive started choking 

“little girl don’t play with me” Naomi clipped out Olive got pissed the whole house started to shake Naomi let go looking around

“Olive what happened you couldn’t  breath?” Dean asked running into the dining room  looking his sister over checking making sure she was breathing alright

“She was choking me!” Olive said 

“I wouldn’t John she's lying!” Naomi said

“my daughter doesn’t lie ever! It’s kind of her thing” John said 

“sweetheart are you alright?” Jimmy asked softly knowing  she wasn't but he still asked 

“no!” She said crying 

“I got you!” Jimmy said hugging her 

“touch her again and I’ll kill myself!” Jimmy said shaking with anger taking Olive out of the room. 

“I didn’t!” Naomi said 

“actually she did sir! I saw the whole thing!” Ellen said walking into the dining room

“get out!” John said not hesitating

“what?” Naomi asked

“you heard me get out of my house! I will be filing an annulment of this marriage! It was meant to show that we could all get along but you choked my daughter not to stop her from doing harm but because you felt like you weren’t respected!” John said 

“she’s a menace everyone walks on eggshells around her,” Naomi said

“no one does that, you haven't been her long enough to know anything about Olive you see horns and think she's something she not” Ellen said “we treat her with respect! She respects us! We know how to handle the mood swings and her powers! You came in demanding a little demon who lost her mama to respect you like you are her mama but your not” She added 

“I… where is she I’ll apologize” Naomi said 

“I still want you gone I won’t tolerate you abusing my children especially Olive” John yelled 

“please John give me one more chance I don’t even know why I did it I let my emotions get the best of me,” Naomi said

“I’m gonna leave it up to Olive!” John said. 

“Olive my love look at me!” Jimmy said tilting her chin up when they were out in the hall 

“I’m ok” She said looking at him, he wiped her tears away with his thumb 

“I’m sorry I panicked I was trying to summon you or Dean” She said

“baby, don't ever apologize for defending yourself!” Jimmy said

“Olive?” Cas asked timidly not wanting to interrupt but John and sent him to bring Olive and Jimmy back into the room

“oh Cas!” She said hugging him worried she may have scared him 

“I’m sorry if I scared you!” She said

“I’m ok!” He said smiling 

“your dad wants you to come back!” Cas said she nodded and followed Cas with Jimmy in tow. 

Naomi was pacing the room when Olive walked back in with Cas and Jimmy 

“Olive..”

“don’t! You have no idea how hard this is for me and my brother! Our mother hasn’t even been gone that long and you waltz in here and act like head bitch! You aren’t and you never will be! Now if dad wants to keep you that’s fine because I love my father and I want him happy but remember you try anything like that to any of us again and I won’t hesitate to make your head explode” She said “I'm hungry” she added looking at Jimmy 

“we can eat baby!” He said smiling at her proud that she didn't use her powers but her words to say what she was feeling.

“Ellen will you bring the food in please!” John said 

“yes sir!” She answered Naomi sat down, after breakfast John took Olive to his office,

“my sweet demon if you don’t feel safe with her she’s gone!” John said

“do you love her?” Olive asked not really wanted to know they answer to the question but she asked any ways

“not as much as loved your mother but yeah I do!” John said 

“daddy this is hard for me and Dean. Dean doesn't say anything because he wants to keep the peace but I can't just pretend, I won't acted like I like her because I don't ” Olive said

“I know and I should have just told you that’s on me And I understand I don’t expect you to love her or her to replace your mother no one will do that ok?” John said 

“yeah dad thank you!” Olive said

“how are you and Jimmy?” John asked 

“we are good dad! Really good, he so understanding and wonderful, why do you keep asking?” Olive said smiling 

“he’s a good guy!” John said 

“Dad is there a reason you really wanted jimmy and I to complete the bond? And you keep asking if we are alright” Olive asked John didn’t look at her, 

“dad, I asked you a question!” She said

“I know I’m trying to figure out how to answer!” He said 

“how about don’t lie, I don’t lie to you!” She said

“I want you to bond because he keeps you calm! Demons like you need a strong bond to keep them in control you’ve always had Dean but the older you get, I feel like that bond is fading!” John said

“Dad, Dean and I are more alike than you know! And we have an unbreakable bond, we are closer than ever!” She said 

“ok I’m sorry I hid that from you!” John said

“I’m sorry I made you tell the truth!” She said feeling a little bad for using her powers on her dad

“it’s ok! Go on! Go be with your angel while I sort out mine” John said. 


	8. Chapter 8

**Chapter 8**

 

They returned to school the following day Cas and Dean hand in hand 

 

“Not you too” Lisa said 

 

“Yes me too, I happen to like him” Dean said smiling Cas blushed 

 

“This is a disgrace, your sister bond with one and now you” She spat walking away

 

“We are popular” Dean said smiling at Cas

 

“If this is gonna make you lose friends we don’t have to…” 

 

“Cas I like you a lot and I don’t want to not be with you,  And if I lose my friends they weren’t friends in the first place,” Dean said smiling Cas blushed a deep scarlet and turned his head 

 

“Alright let’s go see where Jimmy and O took off to” Dean said Cas nodded. 

 

Jimmy and Olive were in the headmasters office not because they were in trouble but to work out the logistics of Olives needs and what it means to have a bonded pair at school

 

“Your father called me and told me that you finished to bond and what that means for you Olive to no longer be a virgin” The Headmaster said Olive blushed embarrassed at the fact that she was having this conversation 

 

“Now normally we have a absolutely no sex rule but your dad said you know a spell to soundproof the room!” He said 

 

“Yes I know the spell it’s simple not much magic goes into it!” She said 

 

“Good I'm gonna need you to do that, you’re dismissed!” He said they left the room, 

  
  


“Baby bro found a mate!” Gabriel said excited for his brother

 

“Hello Gabriel!” Jimmy said

 

“Welcome to the family!” Gabriel said hugging Olive

 

“Thank you Gabriel!” Olive said hugging him back 

 

“You should know Dean and Cas are a thing now!” Jimmy said 

 

“Raphael is going to shit his pants!” Gabriel said laughing 

 

“Does he not like us?” Olive asked 

 

“Not really he tolerates demons for the angels but other than that he doesn’t really care for demons!” Gabriel said Olive nodded 

 

“Well Yule should be fun!” She said 

 

“Oh yeah! Never a dull or sober moment in the Novak house!” Gabriel said

 

“Can we not talk about this now?” Jimmy said not wanting to worry Olive about their next holiday together

 

“Yeah go on you crazy kids” Gabriel said. 

 

They headed back down the hall to their room 

 

“Jeez don’t you knock” Dean said pulling away from Cas 

 

“Can soundproof the room?” Olive asked

 

“So headmaster ok with your need to get laid?” Dean asked winking 

 

“Oh my god Dean grow up!” Olive said placing the sigils around the room 

 

“No really?” Dean asked 

 

“Yeah dad called him but we need a thing so you’ll know if we are ya know or you guys wanna” Olive said Cas blushed, there was a knock on the door 

 

“Winchester” Pamela said 

 

“Which one?” They asked

 

“Olive” She said

 

“Can I help you?” She asked 

 

“The headmaster said you were casting a soundproof spell on your room I need to see it” She said 

 

“Ok” Olive said stepping back 

 

“I just want to say I’m not against angels and demons bonding” Pamela said 

 

“I don’t care if you were” Olive said putting up a sigil on the door Pamela nodded 

 

“Sorry Olive doesn't lie!” Dean said 

 

“You don’t?” She asked

 

“Nope, it’s a horned demon thing we don’t lie we can omit the  truth or just not tell you something but an outright question I don’t ” Olive said finishing the sigil, 

 

“Alright a few words of Latin and we are good, can one of you go out?” Olive asked 

 

“I’ll go” Jimmy said kissing her as he went. Olive did the spell 

 

“Jimmy you can come back in” Olive called nothing 

 

“Good it worked” Olive said 

 

“About this, you guys know it's just for you and Jimmy right?” Pamela said 

 

“Yes we know” Dean said 

 

“Olive?” She asked 

 

“Yes I know” She said not looking at Pamela

 

“I really don’t wanna talk about my brother having sex can we drop this please!” Olive said 

 

“Yes of course I’m sorry!” Pamela said Jimmy walked back in 

 

“Did it work?” He asked 

 

“Yeah jimmy I call you” Olive said with a smile he smiled back 

 

“Ok I’m gonna go” Pamela said leaving the room. 

 

“Alright new sleeping arrangements” Dean said 

 

“What were you thinking?” Olive asked sitting on the floor in Jimmy’s lap, 

 

“I think you and Jimmy are sharing a bed right?” Dean asked 

 

“Yes” They said 

 

“Ok that I should sleep in Jimmy’s bunk and that way if you guys wanna ya know” Dean said 

 

“Ok” Olive said distracted, finding Jimmy's jawline way more interesting than what dean was talking about

 

“That’s fine with me, we can get clean sheets and stuff” Jimmy said looking a Dean, 

 

“Can you guys leave?” Olive said 

 

“Yep” Dean said pulling Cas behind him, 

 

“Olive we were trying to figure out the sleeping arrangements” Jimmy said 

 

“I know but we can figure that out later and we haven’t yet today and I need to” She said kissing his jawline 

 

“Ok baby I’ll take care of you” Jimmy said kissing her. 

 

Cas and Dean made their way to the dining hall to get a snack, 

 

“Hey!” Charlie said 

 

“Hey!” Dean said giving her a hug 

 

“So you two are the talk instead of your sister!” Charlie said

 

“Better me than her I can’t blow up the school with my mind!” Dean said with a laugh 

 

“Yeah you guys are both hot so you know all the girls are jealous!” Charlie said

 

“Are you jealous?” Cas asked 

 

“No I'm jealous of Jimmy” Charlie said Cas nodded

 

“I’m doing movies if you guys wanna come hang, bring Jimmy and Olive” Charlie said 

 

“We will as soon as they are done!” Dean said 

 

“Done with what?” She asked confused  

 

“Nevermind we will bring them!” Cas said with a laugh

 

Cas and Dean sat in the dining hall for a while before heading back to the room to get Olive and Jimmy for movies in Charlie’s room

  
  


“I don’t think I’ll ever get tired of this!” Olive said laying her head on Jimmy chest 

 

“No baby I don’t think I will either” He said kissing the top of her head

 

“Are you guys done?” Dean asked opening the door a crack 

 

“Yeah you can come in and that would have been really awkward if we weren't” Jimmy said with a chuckle 

 

“Hey Charlie wants us all to go hang out in her room, watch movies and we need some kind of system for this” Dean said

 

“Ok we gotta get dressed so we will meet you down there” Olive said 

 

“Yeah you do that” Dean said walking away

 

“Hey Dean thank you” Olive said meaning it 

 

“Anytime sis” He said with a smile. 

 

Olive and Jimmy got dressed and headed to Charlie’s room 

 

“Can't get angel pussy so you go after demon pussy instead?” Cole asked

 

“Leave us alone” Olive said growled defending Jimmy 

 

“No I really wanna know! You could have a strong thick demon cock but you go for a pansy Angel! I bet he can’t even find the right hole” He said Olive looked at Jimmy how nodded

 

“Are you jealous? Jealous with a tail that short and tiny wings” her eyes flicked black she sniffed his neck he swallowed, her tail snaked up around her arm the tip brushed his hair, it wanted to be part of the teasing “You couldn't handle me” she whispered eye flicking back to green she grinned and walked away.

 

Cole swallowed loudly and adjusted himself, his friends started laughing 

 

“Shut up!” He said storming away. 

 

Jimmy just shook his head and followed Olive she was amazing, she was shy and badass all at the same time 

 

“Olive my love” Jimmy said 

 

“Was that too much?” She said 

 

“Nah baby I know how you feel about me, you are amazing you know that?” He said 

 

“I'm glad I didn't make you upset” She said blushing 

 

“We are mated for life and you still blush when I compliment you” Jimmy said with a smile

 

“I can do what I want” She said knocking on Charlie’s door

 

“Look at you all glowing” Charlie said Olive smiled going into Charlie’s room 

 

“Disgusting” The angel said leaving not before giving Jimmy a look 

 

“What’s her problem?” Olive asked 

 

“We used to date, She was awful, keep trying to get me to bond with her but I didn’t want to so one day she touched me and nothing happened!” Jimmy said

 

“You said it only works if you like each other, so you didn’t really like her?” Olive asked 

 

“I did just not enough to bond with her! Not like you!” Jimmy said cupping her cheek

 

“You two are gonna give me a toothache!” Charlie said they all laughed

 

“Movie time!” Charlie said turning on the TV and DVD player

 

“How did you get a tv? I thought we weren't aloud to have tvs” Cas asked

“The donation my parents sent to the school helped” She said it would explain everything.

 


	9. Chapter 9

Olive fell asleep watching the movie Jimmy kissed her head 

 

“Aren’t you guys cute” Charlie teased

 

“I’m gonna take her back to our room” Jimmy said 

 

“You can stay lay her on my bed” Charlie said getting up so Jimmy could lay Olive down, 

 

“She’s ok?” Charlie asked 

 

“yeah she just naps while we watch movies it relaxes her” Dean said pulling Cas into his lap, kissing the back of his neck, Cas’ breath hitched 

 

“if you wanna use the room I think now would be the time, because when she wakes…” they were already out the door before jimmy finished his sentence. Charlie laughed and looked at Jimmy

 

“the room is soundproof” Jimmy said 

 

“what’s it like being her?” Charlie asked

 

“like being wrapped up in a shy, cuddly hurricane” Jimmy said with a fond smile 

 

“that sounds terrifying” Charlie said 

 

“it’s exciting” Jimmy said smiling at Olive. 

 

“But really is she amazing as she seems?” Charlie asked 

 

“yeah she is! I’ve never met anyone like her, she fierce, strong and loyal. She’s powerful, kind and beautiful! And I wouldn’t want to be mates to any other demon or angel!” Jimmy said. 

  
  


Cas and Dean were kissing as the door shut behind them 

 

“Cas” Dean said as Cas kissed down his neck 

 

“I’ll take care of you” Cas said kissing down Dean's neck

 

“no baby that’s not what I’m talking about” Dean said breathy 

 

“what?” Cas said pulling away 

 

“I wanna bond with you” Dean said 

 

“Dean that’s not something taken lightly” Cas said 

 

“I know its not!.... I…. I’ve never felt ….. dammit” Dean said 

 

“go on Dean” Cas said

 

“I just.. I have been with a lot of demons and I never felt anything for them what I feel for you! I love you Cas! I love you and I don’t ever wanna lose you” Dean said cupping Cas’ face between his hands 

 

“please bond with me” He added 

 

“I love you too and I feel the same way, and we should definitely bond be maybe not here at school because we will get in trouble!” Cas said

 

“good point, on break” Dean said 

 

“yeah but can we before Olive wakes up and needs the room!” Cas said Dean kissed him. 

  
  
  


Olive slept while Charlie and Jimmy watched a movie 

 

“you’re not scared of her?” Charlie asked 

 

“not really, it can be scary but I know she’ll never hurt me so no I’m not scared of her” Jimmy said the door opened 

 

“you're still here?” The angel asked 

 

“yes Hannah I’m still here with my mate” Jimmy responded 

 

“I don’t understand how you could do it with one of them let alone a horned demon at that” Hannah said, Jimmy sighed 

 

“Do not insult my mate! She’s amazing, she treats me like a king when all you ever did was treat me like shit so don’t get mad because I didn’t bond with you! I never loved you, which is why I never said it to you!” Jimmy said Olive woke up when Jimmy raised his voice

 

“Jimmy are you ok?” She asked 

 

“yes my love I’m fine, Come on let’s go get you a snack” Jimmy said 

 

“thanks Charlie for movies even though I slept” Olive said rubbing her eyes

 

“anytime” She said smiling. 

 

“Jimmy what happened?” Olive asked through a yawn

 

“Hannah was just being jealous that’s all!” Jimmy said Olive nodded her tail rubbed his face

 

“I’m ok” He said with a laugh

 

“disgusting! How could you really your father and brother run the angel faction!” 

 

“Uriel” Jimmy said 

 

“she’s scum, demon scum” Uriel said 

 

“did you just insult me mate?” Jimmy asked

 

“yes what are you gonna do about it?” Uriel asked Jimmy punched him hard splitting Uriel's lip making him spit blood

 

“jimmy stop” Olive yelled Uriel punched him back with a gush of blood down Jimmy face 

 

“I said stop!” Olive yelled the both froze mid punch

 

“Olive” Jimmy said straining to move

 

“no, I won’t stand here and watch you pumple each other!” She said 

 

“Thank you  Miss Winchester, You can let them go” Headmaster said she released them 

 

“both of you my office Olive head back to your room, Jimmy will be back to you soon” He said she nodded and walked away towards her room. 

 

“O! What happened?” Dean asked the second Olive walked into the room 

 

“Uriel and Jimmy got into a fight I had to use my powers to stop them!” She said sniffing wiping her eyes 

 

“it’s ok Jimmy will understand!” Cas said hugging her 

 

“they were fighting about me!” She said more annoyed than anything 

 

“tell me what happened?” Dean said 

 

“we went to get a snack and Uriel called me demon scum, Jimmy got mad and punched him! So Uriel punched back and I pretty sure broke jimmy’s nose” She said 

 

“well it sounds like something I would do for you!” Dean said

 

“it’s not that he was fighting it’s that he didn’t stop when I asked them to! I had to freeze both of them, I didn't even know I could do that” She said 

 

“you’re upset you used your powers on Jimmy!” Cas said she nodded “if he’s mad he’s stupid “

  
  


Back in the headmasters office, 

 

“What was the fight about?” Headmaster asked 

 

“he called Olive demon scum” Jimmy said sounding stuffed up from his broken nose 

 

“that’s what she is” Uriel said nursing a split lip and bloody nose

 

“first racism will not be tolerated, Fighting won’t be tolerated but James removing you from Olive would be horrible even painful for her and I won’t do that so for the next week you both will serve dinner together” Headmaster said 

 

“I would include breakfast but that won’t work for Olive” He said

 

“what does it matter for her” Uriel asked 

 

“she has special needs” Jimmy said Uriel shook his head 

 

“disgusting” He said

 

“you’re both dismissed” Headmaster said. 

 

“You insult Olive again and you'll regret it” Jimmy said walked towards his room, 

 

When he opened the door Olive tackled him to the ground pinning him just inside the door

 

“I’m so sorry” She said worried he would be mad she used her powers on him 

 

“baby it’s ok I understand” He said running a hand down her back 

 

“why aren’t you mad?” She said sound surprised

 

“because I acted irrationally, you told me to stop and I didn’t I would have done it too” Jimmy said holding her 

 

“were you expecting a fight?” He asked 

 

she nodded into his neck

 

“we can fight if you want” He said softly 

 

she shook her head 

 

“will you let me up?” He asked 

 

“sorry” She said climbing off him 

 

“What did Headmaster say?” She asked 

 

“Uriel and I have to serve dinner all week” Jimmy said she nodded 

 

“where Dean and Cas?” Jimmy asked 

 

“Went to the dining hall” She said

 

“let’s go” He said

 

“you need to wash your beautiful face” She said he nodded. 

  
  
  



	10. Chapter 10

 

 

**Chapter 10**

 

Everyone rolled out of bed late the next morning scrabbling to get ready, tripping over one another trying to get what they needed to start class,

 

"Whos turn to set the alarm?" Dean asked annoyed by the fact that they were all late

 

"It was yours," Olive said pulling a shirt on over her head not really caring about privacy at the moment

 

"No it wasn't," said Dean he always set the alarm when it was his turn, they took turns setting the alarm to make sure everyone was up at the same time, and there weren't multiple alarms going off at the different time

 

"Who cares, let's go," Cas said, opening the door everyone filled out running to their classes only about 15 minutes late.

 

Gabriel gave them a look when they walked in Olive looked flustered, and Jimmy's shirt was on inside out,

 

"Nice of you to join us," Gabriel said

 

"Sorry we all overslept, someone forgot to set the alarm," Olive said annoyed everyone was looking at them think they were later for another reason.

 

"Don't let it happen again, we were just discussing Yule?" Gabriel said smiling,

 

It was the next big holiday the first time Olive and Dean were going to meet the rest of Cas and Jimmy's family Olive was scared what if they did like her, what if they didn't like Dean she was starting to panic thinking about all the things that could go wrong.

 

"Olive?" Gabriel asked

 

"I'm sorry, what was the question?" Olive asked

 

"What are the symbols of yule?" he repeated.

 

"The yule log, a small yule log with three candles if you don't have a fireplace, evergreens, holly, mistletoe, poinsettia and some other stuff I can't think of right now," Olive said shifting in her seat and rubbing her temples

 

"Olive are you alright?" Gabriel asked

 

"I didn't…. We woke up too late" she said

 

"Go and come back," Gabriel said, knowing she was talking about her herbs, Jimmy had explained everything to him, so he was in the know.

 

Olive hurried to her room looking for the premixed herb Dean keeps ready for her, she couldn't find them, there was no way they were out both Dean and Jimmy have been making sure she was well stocked, she started to panic she needs them she promised she wouldn't miss a dose they were going to kick her out, then the whole plan would be shot.

 

"No, no" she was saying over and over as she tore the room apart trying to find her herbs, she ran out of the room, she needed to calm down, she could handle this no big deal just go to the healers office get some more than go to the Headmaster and let him know, that's what she needed to.

 

The healer wasn't in her office there was a sign that said she was out for the day, Of course, she was Olive thought to herself, no need to panic a summon Dean she would just go to the Headmaster's office he will know what to do, when she got to the office the receptionist said he was in a meeting,

 

"I don't care that he is in a meeting I need to see him now," she said

 

"You are going to have to wait," he said

 

Olive took a deep breath trying to steady herself, she was not gonna freak out that's what they want whoever took her stuff, and she wasn't going to let them win, she sat down in the chair sent a text to Jimmy and Dean to let them know what was going on, Jimmy showed first Gabriel sent him to be with her to make sure she was alright. Finally, after about fifteen minutes Headmaster came out of his office with the healer

 

"Miss. Winchester, Mr. Novak what can I do for you?"

 

'Someone stole my herbs" Olive said

 

"Are you sure?" he asked.

 

"Ya I'm sure," she said

 

"I'll get you some more Mr. Novak can bring them to you," the healer said

 

Jimmy followed her, saying he would be back soon.

 

The Headmaster took Olive into his office to talk about what happened,

 

"How do you know they were stolen?" he asked

 

"There was more than enough last night when we went to bed, Dean gave me my nighttime dose, and we went to sleep. This morning we got up late, so we ran out of the room, Gabriel sent me back to take some because I didn't get a chance to this morning. Dean keeps them in his desk he is more organized than I am and when I got there, they were gone the whole batch he had mixed, the free ones even my ones for pain" she said trying to keep it together.

 

"I will look into, and if anything happens we know why no fault of yours," he said dismissing her

 

Jimmy met her in the hallway herbs in hand, they headed back to their room.

 

"Who would steal these? They have no purpose for anyone else," Jimmy said, pulling out Dean's notebook for mixing the herbs when he is away.

 

"I don't know, but headmaster said he would look into it, but I think we should get a safe, can't have people stealing we should also lock the door when we are out," Olive said taking the herbs from Jimmy

 

"What do they taste like?" Jimmy asked pointing

 

"Kind of sweet, mom mixed in something to make it taste better. Dean used to put it in my food like I didn't know" she said

 

"Ya know we don't have to go back," he said, wrapping his arms around her waist.

 

"Oh really?" she said, wrapping her arms around his neck.

 

"Really," he said with a smile.

 

 

Dean was worried when he didn't hear back from Olive, but there was nothing he could do while in class, and there was a chance she was with Jimmy by the lust he was feeling right now. He texted Olive again this time she answered letting him know she was on and got more of what she needed. Dean breathed a sigh of relief, knowing that Olive wouldn't lose her cool and proud that she handled everything without him today.

 

Olive called her Dad to ask if he would get them a safe for their room since someone came into their room uninvited, he was more than happy to do it and was proud of Olive for keeping her cool and not hurting anyone when she could have, they headed to the dining hall after skipping a few of their classes worse thing they would get detention and have to clean up and help the kitchen staff after dinner.

 

"Miss Olive?" a demon asked.

 

"Can I help you?" Olive asked

 

"You skipped my class today," he said

 

"I'm sorry, who are you?' she asked not recognizing the teacher

 

"I'm the new demons studies teacher Mick Davis," he said

 

"I'm sorry, I had some stuff to take care of," she said

 

"I expect to see both of you tomorrow," he said walking away

 

Jimmy laughed Olive joined what were they going to say they skipped class to have sex, Jimmy lead Olive to the lunch line to get their food and listen to the endless whispers of their fellow students talking about them,

 

"I swear it's like they want me to do something," she said

 

"Ignore them, they are stupid and petty," he said loading his plate with food

 

"Hey, you want pie?" Olive asked

 

"No," Jimmy said

 

"More for me," she said grabbing two slices

 

Jimmy spotted Cas and Dean sitting at a table not too far from the door and headed over they were in a heated whispering conversation but stopped when they saw Olive and Jimmy,

 

"Don't stop on our account" Olive said sitting down next to Dean

 

"Olive I think more than you herbs are missing from the room," Cas said

 

"What else is missing?" she asked.

 

"Mom's ring," Dean said

 

"Are you fucking kidding me?' she said

 

"I took it off to shower and then forgot about it this morning as we were running out" Dean said with tears in his eyes, his Dad gave him his mom's wedding band after she dies he only took it off when he showered not wanting to lose it, but to have someone steals it that was too much for Olive

 

"I'm so tired of this shit! The Headmaster doesn't care what happens to demons, anyone can do anything this school is a joke" Olive said her eyes flashing black and green as she tried to control her angry

 

"Fuck it," she said, giving in to her powers.

 

"Everyone stop!" she yelled. They turned on command.

 

"Olive don't," Dean said knowing what she was going to do if no one else was going to, she was gonna find out who stole their stuff

 

Olive looked at him and smiled.

 

"I'm done being nice," she said Jimmy didn't say anything in truth he was tired of the Headmaster not doing anything to help with all the name-calling and harassment not only they have suffered but everyone else too

 

"Olive what are you gonna do?' Cas asked

 

"Find out who stole our stuff," she said

 

"Olive please stop….." Charlie said walking up to their table

 

"Don't fight, tell me I'll keep you safe" Olive said

 

"Hannah and Uriel they said they would hurt me, I'm not like you I can't," she said tears falling

 

Olive let her go Charlie breathed a sigh of relief, Dean hugged Charlie as she sobbed into his chest he reassured her they weren't mad at her and Olive only wanted the truth and never meant to hurt her. Olive shook with anger they used her friend against them Charlie was kind and trusting, and they threatened her Olive wasn't having any of it, she stood on the table Jimmy watched kind of curious as what was going to happen,

 

"Jimmy, aren't you going to stop her?" Cas asked Jimmy shook his head

 

"Enough is enough Cas, too much bullshit," Jimmy said his eyes glowing blue joined Olive on the table,

 

"Hannah, Uriel you got a problem with us than come and get us" Olive said jumping off the table the teachers and staff where trying to move in to stop what was going to happen but Olive was holding them in place, Hannah and Uriel looked at each other and set the stuff on the table and backed away very slowly.

 

"Olive what are you doing?' John asked Olive looked up

 

"Who called you?' she asked

 

"The Headmaster is the only one not here," John said

 

"He wasn't going to do anything about it," she said

 

"To the office everyone," John said giving Olive a smirk

 

They all headed to the Headmasters office Charlie apologizing for her part in the stealing, Olive let her know that she was forgiven and she understood why she did it, and they were still friends if Charlie always wanted to be friends with her, she said she did. Jimmy was trying to figure out how he tapped into his own powers he never used them except the healing, Cas was worried they were all going to be expelled, as they entered the Headmaster's office, he was pacing.

 

"Olive, you can't…." she cut him off.

 

"I can and I will, In fact, I think you are done being headmaster," she said smiling letting her powers take control

 

"I won't leave. I love this school! And the students" he said

 

"Oh you will, and Gabriel will take over, Pamela will take over his class," she said

"Olive what are you doing?' John asked

 

"Cleaning house, now tell me, Victor, do you really like being headmaster?" she asked, smiling.

 

"Olive enough," Jimmy said she looked at him

 

"No, it's not Jimmy, how much longer do we have to put up with bullshit because he doesn't want to cause conflict?"

 

"Fine just don't make his head explode I can't heal that," he said

Olive smiled at the Headmaster he looked worried

 

"Answer my question," she said

 

"I hate it, there's always someone complaining about you two I am tired of it," he said looking horrified he said it out loud

 

"Told you Dad," she said

 

Dean laughed Cas looked at him like he was crazy this was insane Olive has lost her mind today using her powers on the Headmaster.

 

"I think my daughter is right you should go," John said

 

"I can't believe I told……" his eyes rolled in the back of his head and slumped down on the desk

 

"Olive what did you do?" Hannah asked

 

"That wasn't me I let him go after he admitted to not wanting to be here that was someone else," she said

 

"Everyone he just dropped dead" Olive said

 

They all repeated what she said in a robot voice, Hannah went had got the headteacher who happened to be Gabriel, Uriel went and got the healer Cas and Jimmy took Charlie back to her room,

 

"Will they remember?" John asked

 

"Dad, I know what I am doing," Olive said, "But I didn't do that, that was weird."

 

"How did you tap into Jimmy's powers?" Dean asked

"It's the bond we created he doesn't realize I am slow corrupting him," she said, "he is giving in to his darker temptations, you'll do it to Cas as soon as you bond with him and we will have the twins of one of the most powerful angel's faction."

 

Dean smiled at his sister he loved how wicked she could be.

 

Gabriel walked in with the healer, who looked the Headmaster over and proclaimed him to be dead, Gabriel called his brother to see if Victor had any family so they could retrieve his remains, Raphael informed Gabriel he would take over as Headmaster, and they would find a replacement for his class, Gabriel sent all the kids to their rooms so they could keep everything under wraps for now.

 

Dean and Olive said goodbye to their Dad and headed to their room,

 

"Do you think he knows?" Dean asked

 

"Nope, he would have taken us out by now," Olive said, "no one threats his seat, not even his own kids, so we will keep it quiet for now, and when the time comes we will make our move."


	11. Chapter 11

 

**6 month earlier**

 

Olive, Dean, and Mary had decided to come up with a plan to unseat John at leader of the demon faction he was trying to control the demons too much Mary and Olive were special they were the daughters of Lilith needed to use their gifts but John suppressed them it made them crazy when the suppression wore off or killed them if they weren’t strong enough to fight off the effects but Mary made sure that Olive wasn’t subjected to the same treatment she was, she altered Olives herbs making sure it was still possible for her daughter to carry out their mission of taking over all the faction both angel and demon.

 

“Olive my little demon,” Mary called as she walked past her room.

 

“Yeah, mama,” Olive called back.

 

“Come here I wanna talk to you about something important,” she said

 

“What’s up, mama?” she asked, walking into her mom’s room.

 

“It’s about your brother,” Mary said.

 

“What about Dean?’ Olive asked concerned something had happened.

 

Mary took a deep breath before revealing a secret she’s been carrying for the last 16 years.

 

“Promise you won’t tell him until the time is right?” she said

 

“Of course,” Olive said.

 

“Dean is like us, I cast a spell to bind his powers as much as I could and hid his horns when he was born.”

 

“You did what? Mom, why didn’t you tell him?’ Olive asked.

 

“I didn’t want your father to know, he would have tried to do to Dean what he has done to us, Dean’s not as strong as you and I, we can fight the herbs the effects they make us tired, but we can still fight, the only other demon who knows is Ellen” Mary said

 

“Ok I won’t say anything to Dad or Dean, but dad was there when we were born,” Olive said

 

“Dean came fast, Ellen was with me, we knew you would have horns, but I didn’t expect Dean to have them too, when I saw them I hid him from your father I needed you to know before I leave,” she said.

 

“Mama, where are you going?” Olive asked with a smile.

 

“Oh O! I told you what needs to happen next,” Mary said with a nod.

 

“I know mama, I just don’t want you to go,” Olive said with a thick voice.

 

“Be kind and sweet, but take no shit?” Mary said, kissing her on the forehead.

 

“Now remember you have to find me for the transfer to work.”

 

“I love you,” Olive said.

 

 

After Olive left the room, Mary called Dean to her

“Hey, Mom, what’s up?’ Dean asked.

 

“I need you to watch your sister but make sure the angel knows all about her, your sister should have an easy time seducing him,” Mary said

 

“I always look out for her you know that, and I really don’t wanna think about Olive seducing anyone,” Dean said

 

“I also need you to promise not to get mad when she tells you something, I made her promise to wait,” Mary said

 

“Ok, mom. What is going on?’ he asked.

 

“Nothing Sweetheart, just remember I love you,” she said

 

“I love you too,” he said, leaving the room.

 

 

**9 Months later**

 

“Earth to Olive,” Dean said

 

“Sorry I was thinking about mom,” she said with a sad smile.

 

“It’s ok I know you miss her, I was saying Cas, and I plan on bonding this week,” he said.

 

“That’s awesome, I’m happy for you,” Olive said, smiling.

 

“Is it weird I kinda feel bad that we are using Jimmy like this?” he asked.

 

“No, I actually do love Jimmy,” she said, looking down she wasn’t going to let the guilt getting in the way of their mission.

 

“I know this is hard, and I care a lot about Cas, but it will benefit all of us in the long run,” he said

 

“I know, but now we have Naomi to deal with,” Olive said annoyed that their father married the angel.

 

“What if we get her to attack you again?’ Dean asked

 

“Self defense good call,” she said, smiling.

 

Jimmy and Cas walked in the door looking a little less than happy,

 

“What’s the matter?” Olive asked getting up and walking up to Jimmy

 

“It’s Raphael he is not happy about you both are coming to the Yule celebration,” Jimmy said

 

“That’s too bad, I’ll just have to win him over with my charm or my awkwardness,” she said with a smile.

 

Jimmy took a deep breath; he didn’t know how to tell her that they shouldn’t go to his house for yule.

 

“Can’t we just got to your house?” Jimmy asked

 

“No, now suck it up we are going to your house to meet your dad, and your brother just has to deal with it,” Olive said, shaking her head.

 

Jimmy’s phone chimed Gabriel was at their door,

 

“Hey, Gabriel what’s up?” Olive asked

 

“It’s your dad he’s been hurt, he’s ok but, John is in the hospital,” he said

 

“Oh, ok! Should we go, can we go?’ Olive said starting to panic

 

“Yeah Jimmy will go with you and Cas, they sent a car,” he said

 

“Let’s go,” Dean said, pulling Cas behind him.

 

They pulled up to the hospital Olive put on the distraught daughter face and headed inside it’s not that she didn’t love John she did it was that he was holding back and entire species of demon simply because he was scared they would take over one day and he would rather suppress their powers by feeding them herbs that make them sick if they aren’t strong enough to fight the effects and she couldn’t have her children and her brother go through what she goes through on a daily basis, continually fighting at war with herself hiding who she is to please other people. They made their way to Johns’ room. Naomi was there sitting next to his bed.

 

“What happened?” Dean asked Naomi looked up

 

“He fell down the stairs,” she said her eyes bloodshot and rimmed red from crying.

 

Olive shook her head, she was going with the old he fell down the stairs routine.

 

“What you don’t believe me?’ Naomi said

 

“No, I don’t,” Olive said, leaving the room. Jimmy followed her out of the room.

 

“He will be ok,” Jimmy said, holding her close.

 

“I know he is a tough old demon,” she said, leaning against Jimmy.

 

They visited with John, and he told them he would be home soon, and they should go back to school, John would let them know how he was doing, they reminded John that they were going to Jimmy and Cas’ for Yule.

 

“I forgot about that,” John said.

 

“We are invited too, Raphael and I are old friends,” Naomi said.

 

“And by old you mean you used to screw?’ Olive asked.

 

“Olive!” they all scolded her.

 

“what? it’s just a question” she said looking at everyone

 

“And none of your business,” Naomi said.

 

“So that’s a yes,” Olive said pushing Naomi’s buttons.

 

Naomi got up and walked out, glaring at Olive.

 

“Nice,” Dean said.

 

“Oh, shut up you don’t like her either,” Olive said, looking at Dean.

 

“You don’t have to like her but stop antagonizing her please,” John said

 

“Fine, let us know if you guys are coming,” Olive said

 

“Is something wrong?’ John asked noticing Olive had more attitude than normal

 

“Yeah, how did you fall down the stairs?’ she asked

 

“I got light-headed and fell it does happen,” John said

 

Olive shook her head tears formed she was not gonna cry, but she could lose her dad too.

 

“Olive, don’t, cry I’m ok,” John said, holding out his arms.

 

“I can’t lose you too,” she said, trying to hold back her tears.

 

“I’ll be ok, promise.”

 

“Dad I swear to Lilith if she does something to you,” she said

 

“She’s not going to, now go enjoy you 2 weeks off,” he said, sending the kids away.

 

They walked to the car, their bags were sent ahead Gabriel had taken care of all of that for them they headed to the airport for the two hour flight to Cas and Jimmy’s home, Dean hated flying which Cas thought was amusing but kept Dean distracted the whole time, Olive offered to just used her powers and knock him out but he opted not to, when they finally landed Raphael was there to pick them up,

 

“He is adopted,” Jimmy said.

 

“I wasn’t going to say anything,” she said as they walked up to him.

 

“James, Castiel” Raphael said in a deep voice.

 

“Hi, I’m Olive,” she said, holding out her hand.

 

Raphael looked her up and down.

 

“James, A demon,” he said

 

“Are you judging me?” Olive asked

 

“Do not speak to me in that tone?” he said eyes turning bright blue.

 

“Are you trying to take my voice?” she asked “I’m stronger than you, but cute parlor trick” she added walking to the car Jimmy smiling following her.

 

“I’m Dean,” he said following his sister.

 

Raphael looked him up and down, The drive to their house was tense.

 

“I moved dad in with me,” Raphael said

 

“And our stuff?” Jimmy asked

 

“I have moved you in too,” he said, “separate rooms.”

 

“Ok but we don’t mind sharing a room,” Cas said

 

“I thought with the bonding you might be to be alone,” Raphael said

 

Olive laughed. Jimmy looked at her.

 

“He is pissed about it, and he is pissed dad married Naomi this should be an interesting trip,” she said

 

“Did you read my mind?” Raphael asked pulling up to the mansion

 

“No you project, angers the easiest to pick up on,” she said following Jimmy out of the car.

 

“Boys” the man waiting said

 

“DAD,” they said in unison running to him for a hug.

 

“You bonded, Whos, the lucky angel?” he asked.

 

“Not an angel, Meet Olive Winchester,” Jimmy said standing back,

 

“Did you say Winchester?” he asked

 

“Yes, he did!” Olive said defensively

 

“I’m… I’m sorry I’m Chuck” he said

 

Olive just looked at him.

 

“Why did you assume I would be an angel?” she asked.

 

“Olive let it go,” Dean said

 

“I’m Dean Winchester,” he said introducing himself

“Nice to meet you,” Chuck said

 

He leads everyone inside, Raphael showed them to their rooms which were not decorated he said he wanted Cas and Jimmy to do it to their liking, Olive looked around it was about the same size as her room at home, a king-size bed in the middle of the room made up with pillows and blankets in an awful shade of yellow,

 

“This looks like baby poop,” Olive said 

 

“How do you know what baby poop looks like,” Jimmy asked

 

“We had a baby brother he died,” Olive said

 

“I’m so sorry,” Jimmy said

 

“Thanks, wanna break in the bed?’ she asked he smiled and walked her backward to the bed.

 

Gabriel was downstairs in the kitchen when Olive and Jimmy made their way down.

 

“I was gonna let you know I was here, but I didn’t wanna interrupt,” he said with a wink.

 

“I didn’t think we were that loud” Olive said

 

“No shame in your game?” Gabriel asked

 

“Nope,” she said, popping a grape in her mouth and smiling.

 

Jimmy shook his head at his brother and mate, the two of them were terrible when they were together.

 

“I do have a question for you, do you have a birthmark?” Gabriel asked

 

“You wanna know if I’m the daughter of Lilith?’ Olive asked

 

“Yes, I do?’ Gabriel said

 

“Yes I am my mother’s side,” she said

 

Jimmy looked very confused, but he didn’t wanna interrupt he never really cared what kind of demon she was, he only cared about her and the bond they had before she touched him.

 

“That’s amazing there aren’t many left,” Gabriel said “I have always been fascinated with the daughters of Lilith, and it explains why you are so powerful, is Dean, a son?’ he asked.

 

“Does Dean have horns?’ she asked.

 

“No I guess not, man I was really hoping I’m working on a paper about the importance of demons like you in society and the roles you play,” he said excitedly like a kid in a candy store.

 

“Jimmy, you ok babe?’ Olive asked

 

“Yeah I just thought that order was a myth and I’m bonded to an actual Daughter that’s insane not that it matters, I love you no matter what,” he said.

 

“I love you too, and you can’t change your mind you are stuck with me for life,” she said, smiling. 

 

Dean and Cas finally made their way down to the kitchen they had a glow around them,

 

“Hi,” Olive said smiling at them

 

“Shut up,” Dean said

 

“Looks good on you,” she said

 

“Whatever” Dean said wrapping an arm around Cas.

 

“I am happy,” she said, smiling.

 

Raphael walked into the kitchen, took a deep breath.

 

“Your father and Naomi are here,” he said

 

“They did decide to come,” Dean said

 

“Looks like it,” Raphael said, looking angry, leaving the room.

 

Olive, Jimmy, Cas, and Dean all went to find John and Naomi, guess Raphael had told them the news there was yelling coming from the living room John was in Raphael’s face Gabriel was in between trying to get them to calm down and Chuck was off to the side watching everything go down,

 

“Sit,” Olive said

 

It startled everyone they all sat,

 

“What is wrong with the both of you, you are both adults acting like children,” Olive said Jimmy stifled a laugh.

 

“Undo your hold child,” Raphael said

 

“Make me,” Olive said tilting her head Raphael’s eyes tried turning blue he was giving it a reasonable effort, but Olive was the most powerful in the room, and he knew it, but there was no way Raphael was going to lose to some demon, he gave up.

 

“Are you both done?” she asked John nodded knowing if he tried to fight it would be worse for him,

 

“What was this about?” Dean asked

 

“You and Castiel bonding, I promised him to another” Raphael said

 

“What? You were going to sell me like cattle?” Cas asked

 

“It was for an alliance the demons are planning on taking all of us out and ruling everything,” he said

 

“No, we aren’t, We need an alliance with you” Olive said annoyed

 

“You are wrong child, I know what I heard,” Raphael said, “Your fathers plan to overthrow all of us.”

 

“That’s not my father’s plan, that’s my plan,” Olive said eyes flashing black she looked at Dean

 

“Let go,” she said waving her hand in front of his face, two tiny black horns appeared not much bigger than hers,

 

“You are like mama and me,” she said smile

 

Dean smiled at her “this is what you and mom kept secret?”

 

Olive nodded “Sorry, but we couldn’t let dad know he would have put you on the herbs too and it would have killed you.” she said

 

“You deceitful little brat,” Naomi said trying to use her powers Olive raised an eyebrow

 

“Why did you marry my father? Your powers don’t work on me. I’m stronger I needed to know how far Jimmy would go to protect me,” she asked.

 

Naomi opened her mouth and then closed it not wanting to say, she repeated the action looking like a fish,

 

“Olive stop we can talk about this” Jimmy said

 

“I don’t think you wanna talk about it I think you wanna help me,” she said kissing him his eyes turned blue

 

“Of course my love,” he said smiling at her

 

“How did you do that?” Dean asked amazed at her power

 

“It’s the bond, I noticed it the other day,” she said with a shrug.

 

“I’ll ask you again, why did you want to marry my father?” Olive asked

 

“To unseat him, he needed to be taken out,” Naomi said

 

“You were gonna kill him?” Dean asked

 

“Yes, he should have died when he fell down the stairs,” she said

 

“Told you,” Olive said to John

 

“You bitch” he yelled, then turned his focus back on his kids,

 

John shook his head, his own kids were trying to unseat him he was right Olive did want him out

 

“How long have you been planning this?” John asked.

 

“Moms plan not mine, you are killing us! I am the last true daughter of Lilith because your herbs have either driven us insane or we have killed ourselves to escape it. The rest are hidden like Dean was” Olive said

 

“That’s not true, the herbs just keep the power in check,” John said

 

“No, it doesn’t Why do you think mom killed herself and gave me her powers,” Olive said

 

“This is too much,” Cas said sitting on the couch

 

“Cas I’m sorry,” Olive said

 

“You used Jimmy,” he said

 

“At first, but I do love him,” she said, “I really do.”

 

“He is gonna be pissed when he finds out,” Cas said

 

“He will get over it,” Olive said.

 

Gabriel looked at her

“What are you going to do?” he asked

 

“I wanted to talk to you, but it seems your brother had other ideas about this” Olive said

 

“I have an idea,” Dean said

 

“What?” Olive asked sitting on the couch next to Cas

 

“I say we kill them all, you and Jimmy can rule the Demons, Cas and I can take over the angels,” Dean said

 

“Not a bad idea but I don’t wanna start a war,” she said

“Yeah, but what if angel kills another angel?” Dean said

 

“See this is why I love you,” Olive said we need to make it look like she went after everyone,” she said smiling

 

“Ooh, sis can I try?” Dean asked smiling

 

“Hells yeah you can try,” she said

 

“Are we really doing this?’ Cas asked.

 

“You want to be sold like cattle?” Olive asked

 

“No but do to me what you did to Jimmy,” he said

 

“I have to kiss you,” she said

 

“That’s fine,” he said

 

Olive kissed him his eyes went blue,

 

“So after you kill all of us than what?” John asked 

 

“Daddy don’t worry Uncle Azezal will take over you remember him right,” Olive said

 

“Your Uncle died,” John said

 

“No, Daddy just wanted you to think that,” she said.

 

Dean focused on Naomi and willed her to kill everyone but him, Olive, Jimmy, and Cas, then kill herself while Olive made a frantic call to the police.

 

When the police came Olive was crying covered in blood, Dean held Cas and Jimmy was holding Gabriel,

 

“What happened?” the officer asked

 

“She went crazy,” Jimmy said, “Killed everyone, we tried to hide.”

 

“I, she killed my dad,” Cas said crying

 

“” You are all bonded,” she asked they nodded

 

“Is there anyone you can call?’ she asked

 

“We can call Ellen she’s part of our family,” Dean said

 

 

Olive didn’t say anything, she just sat there staring at her father’s dead body,

 

“O come on we gotta go Ellens here,” Dean said, helping his sister up and out to the car.

 

 

**6 months later**

 

“How are you feeling?’ Ellen asked

 

“SO much better without the herbs, it’s nice to do things and not be so tired,” Olive said

 

“And Jimmy?” she asked.

 

“Better one day at a time, he lost his whole family,” Olive said

 

“Yeah but he’s got you, Cas and Dean,” she said

 

“I know, I just feel bad, but I have good news for him so,” Olive said

 

‘What good news?” Ellen asked

 

“I wanna tell my mate first,” Olive said with a smile.

 

“Oh my Lilith, you are not,” Ellen said

 

Olive just smiled and headed up the stairs to their bedroom,

 

“What are you smiling about?” Dean asked

 

“Come on grab Cas I wanna tell all of you,” she said heading to the room, Jimmy was reading a book when he looked up and smiled

 

“There’s my love, where did you go?” he asked.

 

Dean and Cas walked in.

 

“I went to the doctor for a check-up you know after the herbs and everything, and umm he told me something.”

“Oh my, are you ok?” Cas asked

 

“Yes, Cas I’m fine and so is the baby,” she said

 

“The what?’ Jimmy asked, shocked.

 

“The baby is fine,” she said again Dean grabbed her and pulled her into a hug

 

“I’m gonna be a daddy?” Jimmy asked

 

“Yep,” she said smiling

 

“And we won’t have to worry about the angels and demons not getting along now that uncle Azazel has taken over, then hardly any tension the horned demons have come out of hiding,” Olive said.

 

“I think is it’s a girl we name her Lilith” Jimmy said

 

“I like the way you think, come on time for the meeting, and you know how much I like sitting on the throne,” Olive said.

  


**Notes for the Chapter:**

> There is a part 2 coming Im just working on other stuff first I know the ending seems a bit rushed


End file.
